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  • 1
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    Duke University Press | Duke University Press
    Publication Date: 2024-05-12
    Description: History from the Bottom Up and the Inside Out James R. Barrett rethinks the boundaries of American social and labor history by investigating the ways in which working-class, radical, and immigrant people's personal lives intersected with their activism and religious, racial, ethnic, and class identities. Concerned with carving out space for individuals in the story of the working class, Barrett examines all aspects of individuals' subjective experiences, from their personalities, relationships, and emotions to their health and intellectual pursuits. Barrett's subjects include American communists, "blue-collar cosmopolitans"—such as well-read and well-traveled porters, sailors, and hoboes—and figures in early twentieth-century anarchist subculture. He also details the process of the Americanization of immigrant workers via popular culture and their development of class and racial identities, asking how immigrants learned to think of themselves as white. Throughout, Barrett enriches our understanding of working people’s lives, making it harder to objectify them as nameless cogs operating within social and political movements. In so doing, he works to redefine conceptions of work, migration, and radical politics.
    Keywords: History ; Social History ; History ; United States ; 20th Century ; thema EDItEUR::N History and Archaeology::NH History::NHT History: specific events and topics::NHTB Social and cultural history ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas
    Language: English
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  • 2
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    Duke University Press
    Publication Date: 2024-04-02
    Description: In 'An Aqueous Territory' Ernesto Bassi traces the configuration of a geographic space he calls the transimperial Greater Caribbean between 1760 and 1860. Focusing on the Caribbean coast of New Granada (present-day Colombia), Bassi shows that the region's residents did not live their lives bounded by geopolitical borders. Rather, the cross-border activities of sailors, traders, revolutionaries, indigenous peoples, and others reflected their perceptions of the Caribbean as a transimperial space where trade, information, and people circulated, both conforming to and in defiance of imperial regulations. Bassi demonstrates that the islands, continental coasts, and open waters of the transimperial Greater Caribbean constituted a space that was simultaneously Spanish, British, French, Dutch, Danish, Anglo-American, African, and indigenous.
    Keywords: History ; Colombia ; Haiti ; Jamaica ; Riohacha ; Santa Marta ; Spain ; United States ; Wayuu people ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas
    Language: English
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  • 3
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    Duke University Press | Duke University Press
    Publication Date: 2024-04-02
    Description: In Uneven Encounters, Micol Seigel chronicles the exchange of popular culture between Brazil and the United States in the years between the World Wars, and demonstrates how that exchange affected ideas of race and nation in both countries. From Americans interpreting advertisements for Brazilian coffee or dancing the Brazilian maxixe, to Rio musicians embracing the “foreign” qualities of jazz, Seigel traces a lively, cultural back and forth. Along the way, she shows how race and nation for both elites and non-elites are constructed together, and driven by global cultural and intellectual currents as well as local, regional, and national ones. Seigel explores the circulation of images of Brazilian coffee and of maxixe in the United States during the period just after the imperial expansions of the early twentieth century. Exoticist interpretations structured North Americans’ paradoxical sense of themselves as productive “consumer citizens.” Some people, however, could not simply assume the privileges of citizenship. In their struggles against racism, Afro-descended citizens living in Rio de Janeiro, São Paulo, New York, and Chicago encountered images and notions of each other, and found them useful. Seigel introduces readers to cosmopolitan Afro-Brazilians and African Americans who rarely traveled far from home but who nonetheless absorbed ideas from abroad. She suggests that studies comparing U.S. and Brazilian racial identities as two distinct constructions are misconceived. Racial formation transcends national borders; attempts to understand it must do the same.
    Keywords: History ; United States ; 20th Century ; Social Science ; Ethnic Studies ; American ; African American & Black Studies ; History ; Latin America ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas ; thema EDItEUR::J Society and Social Sciences::JB Society and culture: general::JBS Social groups, communities and identities::JBSL Ethnic studies
    Language: English
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  • 4
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    Duke University Press
    Publication Date: 2022-05-02
    Description: Since the late 1990s, Asian nations have increasingly encouraged, facilitated, or demanded the return of emigrants. In this interdisciplinary collection, distinguished scholars from countries around the world explore the changing relations between nation-states and transnational mobility. Taking into account illegally trafficked migrants, deportees, temporary laborers on short-term contracts, and highly skilled émigrés, the contributors argue that the figure of the returnee energizes and redefines nationalism in an era of increasingly fluid and indeterminate national sovereignty. They acknowledge the diversity, complexity, and instability of reverse migration, while emphasizing its discursive, policy, and political significance at a moment when the tensions between state power and transnational subjects are particularly visible. Taken together, the essays foreground Asia as a useful site for rethinking the intersections of migration, sovereignty, and nationalism.
    Keywords: History ; China ; India ; Japan ; Overseas Chinese ; United States
    Language: English
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  • 5
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    Duke University Press | Duke University Press
    Publication Date: 2024-04-02
    Description: In the early twentieth century, Native American baskets, blankets, and bowls could be purchased from department stores, “Indian stores,” dealers, and the U.S. government’s Indian schools. Men and women across the United States indulged in a widespread passion for collecting Native American art, which they displayed in domestic nooks called “Indian corners.” Elizabeth Hutchinson identifies this collecting as part of a larger “Indian craze” and links it to other activities such as the inclusion of Native American artifacts in art exhibitions sponsored by museums, arts and crafts societies, and World’s Fairs, and the use of indigenous handicrafts as models for non-Native artists exploring formal abstraction and emerging notions of artistic subjectivity. She argues that the Indian craze convinced policymakers that art was an aspect of “traditional” Native culture worth preserving, an attitude that continues to influence popular attitudes and federal legislation. Illustrating her argument with images culled from late-nineteenth- and early-twentieth-century publications, Hutchinson revises the standard history of the mainstream interest in Native American material culture as “art.” While many locate the development of this cross-cultural interest in the Southwest after the First World War, Hutchinson reveals that it began earlier and spread across the nation from west to east and from reservation to metropolis. She demonstrates that artists, teachers, and critics associated with the development of American modernism, including Arthur Wesley Dow and Gertrude Käsebier, were inspired by Native art. Native artists were also able to achieve some recognition as modern artists, as Hutchinson shows through her discussion of the Winnebago painter and educator Angel DeCora. By taking a transcultural approach, Hutchinson transforms our understanding of the role of Native Americans in modernist culture.
    Keywords: History ; United States ; 20th Century ; Social Science ; Ethnic Studies ; American ; Art ; American ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas ; thema EDItEUR::A The Arts::AG The Arts: treatments and subjects::AGA History of art
    Language: English
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  • 6
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    Duke University Press
    Publication Date: 2022-05-02
    Description: Presenting an unprecedented, integrated view of migration in North America, this interdisciplinary collection of essays illuminates the movements of people within and between Canada, the Caribbean, Mexico, and the United States over the past two centuries. Several essays discuss recent migrations from Central America as well. In the introduction, Dirk Hoerder provides a sweeping historical overview of North American societies in the Atlantic world. He also develops and advocates what he and Nora Faires call “transcultural societal studies,” an interdisciplinary approach to migration studies that combines migration research across disciplines and at the local, regional, national, and transnational levels. The contributors examine the movements of diverse populations across North America in relation to changing cultural, political, and economic patterns.
    Keywords: History ; Canada ; Mexico ; United States
    Language: English
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  • 7
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    Duke University Press
    Publication Date: 2024-03-29
    Description: In DISCIPLINARY CONQUEST, Ricardo Salvatore argues that the foundation of the discipline of Latin American studies, pioneered between 1900 and 1945, was linked to the United States’s business and financial interests and informal imperialism. In contrast, the consolidation of Latin American studies has traditionally been placed in the 1960s, as a reaction to the Cuban Revolution. Focusing on five representative U.S. scholars of South America—historian Clarence Haring, geographer Isaiah Bowman, political scientist Leo Rowe, sociologist Edward Ross, and archaeologist Hiram Bingham -- Salvatore demonstrates how their search for comprehensive knowledge about South America can be understood as a contribution to hemispheric hegemony, an intellectual conquest of the region. U.S. economic leaders, diplomats, and foreign-policy experts needed knowledge about the region to expand investment and trade, as well as the U.S.’s international influence
    Keywords: Anthropology ; Anthropology ; Anthropology ; Anthropology ; Argentina ; Latin America ; South America ; United States ; bic Book Industry Communication::J Society & social sciences::JH Sociology & anthropology::JHM Anthropology::JHMC Social & cultural anthropology, ethnography ; thema EDItEUR::J Society and Social Sciences::JH Sociology and anthropology::JHM Anthropology::JHMC Social and cultural anthropology
    Language: English
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  • 8
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    Duke University Press
    Publication Date: 2024-03-26
    Description: 'Thinking Literature across Continents' finds Ranjan Ghosh and J. Hillis Miller—two thinkers from different continents, cultures, training, and critical perspectives—debating and reflecting upon what literature is and why it matters. Ghosh and Miller do not attempt to formulate a joint theory of literature; rather, they allow their different backgrounds and lively disagreements to stimulate generative dialogue on poetry, world literature, pedagogy, and the ethics of literature. Addressing a varied literary context ranging from Victorian literature, Chinese literary criticism and philosophy, and continental philosophy to Sanskrit poetics and modern European literature, Ghosh offers a transnational theory of literature while Miller emphasizes the need to account for what a text says and how it says it. This book highlights two minds continually discovering new paths of communication and two literary and cultural traditions intersecting in productive and compelling ways.
    Keywords: Literature ; Ethics ; United States ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DS Literature: history and criticism
    Language: English
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  • 9
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    Duke University Press
    Publication Date: 2024-04-02
    Description: Between 1750 and 1870 the world faced transformations marked by the rise of industrial capitalism, the fall of European empires in the Americas, and the rise of nations there. 'New Countries' explores how these events transformed the Americas in diverging ways. Up to 1790, Saint Domingue’s sugar and slave economy drove Atlantic trades; then revolutionary slaves made Haiti, freeing themselves and ending export production. New Spain’s silver fueled global trades until Bajío insurgents collapsed silver capitalism and undermined Spanish rule after 1810. The fall of silver left regions from Mexico through Guatemala and the Andes in search of new polities and economies. After 1870 the United States became an agro-industrial hegemon, most American nations turned to commodity exports, and Haitians and diverse indigenous peoples struggled to keep independent lives beyond the reach of industrial powers seeking supplies and markets.
    Keywords: History ; Brazil ; Mexico ; Slavery ; Spain ; United States ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas
    Language: English
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  • 10
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    Duke University Press
    Publication Date: 2022-05-02
    Description: From Skirts Ahoy! to M*A*S*H, Private Benjamin, G.I. Jane, and JAG, films and television shows have grappled with the notion that military women are contradictory figures, unable to be both effective soldiers and appropriately feminine. In Soldiers’ Stories, Yvonne Tasker traces this perceived paradox across genres including musicals, screwball comedies, and action thrillers. She explains how, during the Second World War, women were portrayed as auxiliaries, temporary necessities of “total war.” Later, nursing, with its connotations of feminine care, offered a solution to the “gender problem.” From the 1940s through the 1970s, musicals, romances, and comedies exploited the humorous potential of the gender role reversal that the military woman was taken to represent. Since the 1970s, female soldiers have appeared most often in thrillers and legal and crime dramas, cast as isolated figures, sometimes victimized and sometimes heroic. Soldiers’ Stories is a comprehensive ...
    Keywords: Media & Communications ; Femininity ; Masculinity ; Military ; Nursing ; Rape ; United States ; Women in the military ; World War II
    Language: English
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  • 11
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    Duke University Press
    Publication Date: 2024-03-23
    Description: Chronicling the dramatic history of the Brazilian Amazon during the Second World War, Seth Garfield provides fresh perspectives on contemporary environmental debates. His multifaceted analysis explains how the Amazon became the object of geopolitical rivalries, state planning, media coverage, popular fascination, and social conflict. In need of rubber, a vital war material, the United States spent millions of dollars to revive the Amazon's rubber trade. In the name of development and national security, Brazilian officials implemented public programs to engineer the hinterland's transformation. Migrants from Brazil's drought-stricken Northeast flocked to the Amazon in search of work. In defense of traditional ways of life, longtime Amazon residents sought to temper outside intervention.
    Keywords: History ; Brazil ; Ceará ; Natural rubber ; United States ; thema EDItEUR::1 Place qualifiers::1K The Americas::1KL Latin America – Mexico, Central America, South America
    Language: English
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  • 12
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    Duke University Press
    Publication Date: 2022-05-02
    Description: A NATION ON THE LINE is an ethnographic study of the call center industry in the Philippines and of its workforce composed of young, largely college-educated Filipinos. Padios merges several lines of inquiry about Pacific transnationalism, about the role of affective labor in global markets, and about critique of Filipino exploitation by the United States through economic and military power since independence-- in order to consider how post-colonial and post-industrial changes in the Philippines’ role in global capitalism and culture are brought to bear in everyday life. Padios argues that the call center industry serves as a rich case-study for how Filipinos work within hegemonic dynamics of relational service and an understanding of American consumer culture in ways that figure Filipinos' sense of identity and aspirations at the national and individual levels.
    Keywords: Anthropology ; Customer service ; Filipinos ; Philippines ; United States
    Language: English
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  • 13
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    Duke University Press | Duke University Press
    Publication Date: 2024-04-02
    Description: Published in cooperation with the William P. Clements Center for Southwest Studies, Southern Methodist University. In Land of Necessity, historians and anthropologists unravel the interplay of the national and transnational and of scarcity and abundance in the region split by the 1,969-mile boundary line dividing Mexico and the United States. This richly illustrated volume, with more than 100 images including maps, photographs, and advertisements, explores the convergence of broad demographic, economic, political, cultural, and transnational developments resulting in various forms of consumer culture in the borderlands. Though its importance is uncontestable, the role of necessity in consumer culture has rarely been explored. Indeed, it has been argued that where necessity reigns, consumer culture is anemic. This volume demonstrates otherwise. In doing so, it sheds new light on the history of the U.S.-Mexico borderlands, while also opening up similar terrain for scholarly inquiry into consumer culture. The volume opens with two chapters that detail the historical trajectories of consumer culture and the borderlands. In the subsequent chapters, contributors take up subjects including smuggling, tourist districts and resorts, purchasing power, and living standards. Others address home décor, housing, urban development, and commercial real estate, while still others consider the circulation of cinematic images, contraband, used cars, and clothing. Several contributors discuss the movement of people across borders, within cities, and in retail spaces. In the two afterwords, scholars reflect on the U.S.-Mexico borderlands as a particular site of trade in labor, land, leisure, and commodities, while also musing about consumer culture as a place of complex political and economic negotiations. Through its focus on the borderlands, this volume provides valuable insight into the historical and contemporary aspects of the big “isms” shaping modern life: capitalism, nationalism, transnationalism, globalism, and, without a doubt, consumerism. Contributors. Josef Barton, Peter S. Cahn, Howard Campbell, Lawrence Culver, Amy S. Greenberg, Josiah McC. Heyman, Sarah Hill, Alexis McCrossen, Robert Perez, Laura Isabel Serna, Rachel St. John, Mauricio Tenorio-Trillo, Evan R. Ward
    Keywords: History ; United States ; 20th Century ; Social Science ; Sociology ; History ; Latin America ; Mexico ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas ; thema EDItEUR::J Society and Social Sciences::JH Sociology and anthropology::JHB Sociology
    Language: English
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  • 14
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    Duke University Press
    Publication Date: 2024-03-23
    Description: In 'Dying in Full Detail' Jennifer Malkowski explores digital media's impact on one of documentary film's greatest taboos: the recording of death. Despite technological advances that allow for the easy creation and distribution of death footage, digital media often fail to live up to their promise to reveal the world in greater fidelity. Malkowski analyzes a wide range of death footage, from feature films about the terminally ill (Dying, Silverlake Life, Sick), to surreptitiously recorded suicides (The Bridge), to #BlackLivesMatter YouTube videos and their precursors. Contextualizing these recordings in the long history of attempts to capture the moment of death in American culture, Malkowski shows how digital media are unable to deliver death "in full detail," as its metaphysical truth remains beyond representation.
    Keywords: Media and Communications ; Suicide ; United States ; thema EDItEUR::A The Arts::AT Performing arts::ATF Films, cinema ; thema EDItEUR::A The Arts::AT Performing arts::ATJ Television
    Language: English
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  • 15
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    Duke University Press
    Publication Date: 2024-04-02
    Description: Cuba's first republican era (1902–1959) is principally understood in terms of its failures and discontinuities, its first three decades and the overthrow of Machado seen at best as a prologue to the "real" revolution of 1959. This book brings together scholars from North America, Cuba, and Spain to challenge this narrative, presenting republican Cuba instead as a time of meaningful engagement—socially, politically, and symbolically. Addressing a wide range of topics—civic clubs and folkloric societies, science, public health and agrarian policies, popular culture, national memory, and the intersection of race and labor—the contributors explore how a broad spectrum of Cubans embraced a political and civic culture of national self-realization. These essays recast the first republic as a time of deep continuity in processes of liberal state- and nation-building that were periodically disrupted—but also reinvigorated—by foreign intervention and profound uncertainty.
    Keywords: History ; Anarchism ; Cuba ; Havana ; United States ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas
    Language: English
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  • 16
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    Duke University Press
    Publication Date: 2024-03-28
    Description: Drawing on methods and approaches from anthropology, media studies, film theory, and cultural studies, the contributors to Media, Erotics, and Transnational Asia examine how mediated eroticism and sexuality circulating across Asia and Asian diasporas both reflect and shape the social practices of their producers and consumers. The essays in this volume cover a wide geographic and thematic range, and combine rigorous textual analysis with empirical research into the production, circulation, and consumption of various forms of media. Taken together, the essays offer fresh insights into research on gender, erotics, media, and Asia transnationally conceived. Contributors. Anne Allison, Tom Boellstorff, Nicole Constable, Heather Dell, Judith Farquhar, Sarah L. Friedman, Martin F. Manalansan IV, Purnima Mankekar, Louisa Schein, Everett Yuehong Zhang.
    Keywords: Media and Communications ; China ; Hmong people ; Homosexuality ; United States ; Zine ; thema EDItEUR::J Society and Social Sciences::JB Society and culture: general::JBC Cultural and media studies::JBCT Media studies
    Language: English
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  • 17
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    Duke University Press
    Publication Date: 2024-04-02
    Description: In Musicians in Transit Matthew B. Karush examines the transnational careers of seven of the most influential Argentine musicians of the twentieth century: Afro-Argentine swing guitarist Oscar Alemán, jazz saxophonist Gato Barbieri, composer Lalo Schifrin, tango innovator Astor Piazzolla, balada singer Sandro, folksinger Mercedes Sosa, and rock musician Gustavo Santaolalla. As active participants in the globalized music business, these artists interacted with musicians and audiences in the United States, Europe, and Latin America and contended with genre distinctions, marketing conventions, and ethnic stereotypes. By responding creatively to these constraints, they made innovative music that provided Argentines with new ways of understanding their nation’s place in the world.
    Keywords: Music ; Argentina ; Astor Piazzolla ; Jazz ; Latin ; Latin America ; United States ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas
    Language: English
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  • 18
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    Duke University Press
    Publication Date: 2024-04-02
    Description: Citizenship is often assumed to be a clear-cut issue - either one has it or one does not. However, as the contributors to Citizenship in Question demonstrate, citizenship is not self-evident; it emerges from often obscure written records and is interpreted through ambiguous and dynamic laws. In case studies that analyze the legal barriers to citizenship rights in over twenty countries, the contributors explore how states use evidentiary requirements to create and police citizenship, often based on fictions of racial, ethnic, class, and religious differences. Whether examining the United States’ deportation of its own citizens, the selective use of DNA tests and secret results in Thailand, or laws that have stripped entire populations of citizenship, the contributors emphasize the political, psychological, and personal impact of citizenship policies.
    Keywords: History ; Birth certificate ; Ivory Coast ; Mexico ; Statelessness ; Taiwan ; United States ; thema EDItEUR::N History and Archaeology::NH History::NHB General and world history
    Language: English
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  • 19
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    Duke University Press
    Publication Date: 2022-05-02
    Description: In What’s Left of the Left, distinguished scholars of European and U.S. politics consider how center-left political parties have fared since the 1970s. They explore the left’s responses to the end of the postwar economic boom, the collapse of the Soviet Union, the erosion of traditional party politics, the expansion of market globalization, and the shift to a knowledge-based economy. Their comparative studies of center-left politics in Scandinavia, France, Germany, southern Europe, post–Cold War Central and Eastern Europe, the United Kingdom, and the United States emphasize differences in the goals of left political parties and in the political, economic, and demographic contexts in which they operate. The contributors identify and investigate the more successful center-left initiatives, scrutinizing how some conditions facilitated them, while others blocked their emergence or limited their efficacy.
    Keywords: Political Science ; Left ; Politics ; Political parties ; Europe ; United States
    Language: English
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  • 20
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    Duke University Press | Duke University Press
    Publication Date: 2024-04-02
    Description: 'In We Dream Together' Anne Eller breaks with dominant narratives of conflict between the Dominican Republic and Haiti by tracing the complicated history of Dominican emancipation and independence between 1822 and 1865. Eller moves beyond the small body of writing by Dominican elites that often narrates Dominican nationhood to craft inclusive, popular histories of identity, community, and freedom, summoning sources that range from trial records and consul reports to poetry and song. Rethinking Dominican relationships with their communities, the national project, and the greater Caribbean, Eller shows how popular anticolonial resistance was anchored in a rich and complex political culture. Haitians and Dominicans fostered a common commitment to Caribbean freedom, the abolition of slavery, and popular democracy, often well beyond the reach of the state.
    Keywords: History ; Cuba ; Dominican Order ; Haiti ; Puerto Plata ; Dominican Republic ; Santana (band) ; Santo Domingo ; Spain ; Spaniards ; United States ; thema EDItEUR::N History and Archaeology::NH History::NHK History of the Americas
    Language: English
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  • 21
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-02-16
    Keywords: Chemistry
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Geosciences , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 22
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-02-16
    Description: The comment and response concerning the report of oxidation of methane to methanol by water (Reports, 5 May 2017, p. 523) do not fully capture the implications of thermodynamic limitations. A nonisothermal process in which each cycle requires a large temperature swing and permits only substoichiometric methane conversion surely could not be carried out on any practical scale.
    Keywords: Chemistry
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Geosciences , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 23
    Publication Date: 2018-02-16
    Description: Labinger argues that stepwise reaction of methane with water to produce methanol and hydrogen will never be commercially feasible because of its substoichiometric basis with respect to the active site and the requirement of a large temperature swing. This comment is not touching any new ground, beyond describing the thermodynamic feasibility, thermal cycling, and the role of water as discussed previously. Most important, it does not have a solid numerical basis.
    Keywords: Chemistry
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Geosciences , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 24
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-07-27
    Keywords: Chemistry
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Geosciences , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 25
    Publication Date: 2018-07-27
    Description: Vinyl carbocations have been the subject of extensive experimental and theoretical studies over the past five decades. Despite this long history in chemistry, the utility of vinyl cations in chemical synthesis has been limited, with most reactivity studies focusing on solvolysis reactions or intramolecular processes. Here we report synthetic and mechanistic studies of vinyl cations generated through silylium–weakly coordinating anion catalysis. We find that these reactive intermediates undergo mild intermolecular carbon-carbon bond–forming reactions, including carbon-hydrogen (C–H) insertion into unactivated sp 3 C–H bonds and reductive Friedel-Crafts reactions with arenes. Moreover, we conducted computational studies of these alkane C–H functionalization reactions and discovered that they proceed through nonclassical, ambimodal transition structures. This reaction manifold provides a framework for the catalytic functionalization of hydrocarbons using simple ketone derivatives.
    Keywords: Chemistry
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Geosciences , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 26
    Publication Date: 2018-06-22
    Description: It is commonly assumed that recognition and discrimination of chirality, both in nature and in artificial systems, depend solely on spatial effects. However, recent studies have suggested that charge redistribution in chiral molecules manifests an enantiospecific preference in electron spin orientation. We therefore reasoned that the induced spin polarization may affect enantiorecognition through exchange interactions. Here we show experimentally that the interaction of chiral molecules with a perpendicularly magnetized substrate is enantiospecific. Thus, one enantiomer adsorbs preferentially when the magnetic dipole is pointing up, whereas the other adsorbs faster for the opposite alignment of the magnetization. The interaction is not controlled by the magnetic field per se, but rather by the electron spin orientations, and opens prospects for a distinct approach to enantiomeric separations.
    Keywords: Chemistry
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  • 27
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-06-29
    Keywords: Chemistry
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  • 28
    Publication Date: 2018-12-14
    Description: Theory has established the importance of geometric phase (GP) effects in the adiabatic dynamics of molecular systems with a conical intersection connecting the ground- and excited-state potential energy surfaces, but direct observation of their manifestation in chemical reactions remains a major challenge. Here, we report a high-resolution crossed molecular beams study of the H + HD -〉 H 2 + D reaction at a collision energy slightly above the conical intersection. Velocity map ion imaging revealed fast angular oscillations in product quantum state–resolved differential cross sections in the forward scattering direction for H 2 products at specific rovibrational levels. The experimental results agree with adiabatic quantum dynamical calculations only when the GP effect is included.
    Keywords: Chemistry
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  • 29
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-17
    Keywords: Chemistry
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  • 30
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-17
    Keywords: Chemistry
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  • 31
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-17
    Description: The chemistry of the carbonyl group is essential to modern organic synthesis. The preparation of substituted, enantioenriched 1,3- or 1,5-dicarbonyls is well developed, as their disconnection naturally follows from the intrinsic polarity of the carbonyl group. By contrast, a general enantioselective access to quaternary stereocenters in acyclic 1,4-dicarbonyl systems remains an unresolved problem, despite the tremendous importance of 2,3-substituted 1,4-dicarbonyl motifs in natural products and drug scaffolds. Here we present a broad enantioselective and stereodivergent strategy to access acyclic, polysubstituted 1,4-dicarbonyls via acid-catalyzed [3,3]-sulfonium rearrangement starting from vinyl sulfoxides and ynamides. The stereochemistry at sulfur governs the absolute sense of chiral induction, whereas the double bond geometry dictates the relative configuration of the final products.
    Keywords: Chemistry
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  • 32
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-17
    Keywords: Chemistry
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  • 33
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-17
    Description: With the recent soaring production of natural gas, the use of methane and other light hydrocarbon feedstocks as starting materials in synthetic transformations is becoming increasingly economically attractive, although it remains chemically challenging. We report the development of photocatalytic C–H amination, alkylation, and arylation of methane, ethane, and higher alkanes under visible light irradiation at ambient temperature. High catalytic efficiency (turnover numbers up to 2900 for methane and 9700 for ethane) and selectivity were achieved using abundant, inexpensive cerium salts as photocatalysts. Ligand-to-metal charge transfer excitation generated alkoxy radicals from simple alcohols that in turn acted as hydrogen atom transfer catalysts. The mixed-phase gas/liquid reaction was adapted to continuous flow, enabling the efficient use of gaseous feedstocks in scalable photocatalytic transformations.
    Keywords: Chemistry
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  • 34
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-24
    Keywords: Chemistry
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  • 35
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-24
    Keywords: Chemistry
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  • 36
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-31
    Keywords: Chemistry
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  • 37
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-31
    Description: Intrigued by the potential of nanoscale machines, scientists have long attempted to control molecular motion. We monitored the individual 0.7-nanometer steps of a single molecular hopper as it moved in an electric field along a track in a nanopore controlled by a chemical ratchet. The hopper demonstrated characteristics desired in a moving molecule: defined start and end points, processivity, no chemical fuel requirement, directional motion, and external control. The hopper was readily functionalized to carry cargos. For example, a DNA molecule could be ratcheted along the track in either direction, a prerequisite for nanopore sequencing.
    Keywords: Chemistry
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  • 38
    Publication Date: 2018-09-21
    Description: Phosphorothioate nucleotides have emerged as powerful pharmacological substitutes of their native phosphodiester analogs with important translational applications in antisense oligonucleotide (ASO) therapeutics and cyclic dinucleotide (CDN) synthesis. Stereocontrolled installation of this chiral motif has long been hampered by the systemic use of phosphorus(III) [P(III)]–based reagent systems as the sole practical means of oligonucleotide assembly. A fundamentally different approach is described herein: the invention of a P(V)-based reagent platform for programmable, traceless, diastereoselective phosphorus-sulfur incorporation. The power of this reagent system is demonstrated through the robust and stereocontrolled synthesis of various nucleotidic architectures, including ASOs and CDNs, via an efficient, inexpensive, and operationally simple protocol.
    Keywords: Chemistry
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  • 39
    Publication Date: 2018-09-21
    Description: Here we report an anomalous porous molecular crystal built of C–H···N-bonded double-layered roof-floor components and wall components of a segregatively interdigitated architecture. This complicated porous structure consists of only one type of fully aromatic multijoint molecule carrying three identical dipyridylphenyl wedges. Despite its high symmetry, this molecule accomplishes difficult tasks by using two of its three wedges for roof-floor formation and using its other wedge for wall formation. Although a C–H···N bond is extremely labile, the porous crystal maintains its porosity until thermal breakdown of the C–H···N bonds at 202°C occurs, affording a nonporous polymorph. Though this nonporous crystal survives even at 325°C, it can retrieve the parent porosity under acetonitrile vapor. These findings show how one can translate simplicity into ultrahigh complexity.
    Keywords: Chemistry
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  • 40
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-09-28
    Keywords: Chemistry
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  • 41
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-09-28
    Keywords: Chemistry
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  • 42
    Publication Date: 2018-09-28
    Description: Some of the simplest and most powerful carbon-carbon bond forming strategies take advantage of readily accessible ubiquitous motifs: carbonyls and olefins. Here we report a fundamentally distinct mode of reactivity between carbonyls and olefins that differs from established acid-catalyzed carbonyl-ene, Prins, and carbonyl-olefin metathesis reaction paths. A range of epsilon, zeta-unsaturated ketones undergo Brønsted acid–catalyzed intramolecular cyclization to provide tetrahydrofluorene products via the formation of two new carbon-carbon bonds. Theoretical calculations and accompanying mechanistic studies suggest that this carbocyclization reaction proceeds through the intermediacy of a transient oxetane formed by oxygen atom transfer. The complex polycyclic frameworks in this product class appear as common substructures in organic materials, bioactive natural products, and recently developed pharmaceuticals.
    Keywords: Chemistry
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  • 43
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-09-28
    Description: Alkene aminoarylation with a single, bifunctional reagent is a concise synthetic strategy. We report a catalytic protocol for the addition of arylsulfonylacetamides across electron-rich alkenes with complete anti-Markovnikov regioselectivity and excellent diastereoselectivity to provide 2,2-diarylethylamines. In this process, single-electron alkene oxidation enables carbon-nitrogen bond formation to provide a key benzylic radical poised for a Smiles-Truce 1,5-aryl shift. This reaction is redox-neutral, exhibits broad functional group compatibility, and occurs at room temperature with loss of sulfur dioxide. As this process is driven by visible light, uses readily available starting materials, and demonstrates convergent synthesis, it is well suited for use in a variety of synthetic endeavors.
    Keywords: Chemistry
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  • 44
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-05
    Keywords: Chemistry
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  • 45
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-05
    Keywords: Chemistry
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  • 46
    Publication Date: 2018-10-05
    Description: Photocatalysis based on optically active, "plasmonic" metal nanoparticles has emerged as a promising approach to facilitate light-driven chemical conversions under far milder conditions than thermal catalysis. However, an understanding of the relation between thermal and electronic excitations has been lacking. We report the substantial light-induced reduction of the thermal activation barrier for ammonia decomposition on a plasmonic photocatalyst. We introduce the concept of a light-dependent activation barrier to account for the effect of light illumination on electronic and thermal excitations in a single unified picture. This framework provides insight into the specific role of hot carriers in plasmon-mediated photochemistry, which is critically important for designing energy-efficient plasmonic photocatalysts.
    Keywords: Chemistry
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  • 47
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-12
    Keywords: Chemistry
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  • 48
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-12
    Keywords: Chemistry
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  • 49
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-12
    Description: Single-electron reduction of a carbonyl to a ketyl enables access to a polarity-reversed platform of reactivity for this cornerstone functional group. However, the synthetic utility of the ketyl radical is hindered by the strong reductants necessary for its generation, which also limit its reactivity to net reductive mechanisms. We report a strategy for net redox-neutral generation and reaction of ketyl radicals. The in situ conversion of aldehydes to α-acetoxy iodides lowers their reduction potential by more than 1 volt, allowing for milder access to the corresponding ketyl radicals and an oxidative termination event. Upon subjecting these iodides to a dimanganese decacarbonyl precatalyst and visible light irradiation, an atom transfer radical addition (ATRA) mechanism affords a broad scope of vinyl iodide products with high Z -selectivity.
    Keywords: Chemistry
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  • 50
    Publication Date: 2018-10-12
    Description: Reactions that form a product with the same reactive functionality as that of one of the starting compounds frequently end in oligomerization. As a salient example, selective aldol coupling of the smallest, though arguably most useful, enolizable aldehyde, acetaldehyde, with just one partner substrate has proven to be extremely challenging. Here, we report a highly enantioselective Mukaiyama aldol reaction with the simple triethylsilyl (TES) and tert -butyldimethylsilyl (TBS) enolates of acetaldehyde and various aliphatic and aromatic acceptor aldehydes. The reaction is catalyzed by recently developed, strongly acidic imidodiphosphorimidates (IDPi), which, like enzymes, display a confined active site but, like small-molecule catalysts, have a broad substrate scope. The process is scalable, fast, efficient (0.5 to 1.5 mole % catalyst loading), and greatly simplifies access to highly valuable silylated acetaldehyde aldols.
    Keywords: Chemistry
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  • 51
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-12-21
    Keywords: Chemistry
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  • 52
    Publication Date: 2018-12-21
    Description: Single-molecule magnets (SMMs) containing only one metal center may represent the lower size limit for molecule-based magnetic information storage materials. Their current drawback is that all SMMs require liquid-helium cooling to show magnetic memory effects. We now report a chemical strategy to access the dysprosium metallocene cation [(Cp i Pr5 )Dy(Cp*)] + (Cp i Pr5 , penta-iso-propylcyclopentadienyl; Cp *, pentamethylcyclopentadienyl), which displays magnetic hysteresis above liquid-nitrogen temperatures. An effective energy barrier to reversal of the magnetization of U eff = 1541 wave number is also measured. The magnetic blocking temperature of T B = 80 kelvin for this cation overcomes an essential barrier toward the development of nanomagnet devices that function at practical temperatures.
    Keywords: Chemistry
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  • 53
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-19
    Keywords: Chemistry
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  • 54
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-19
    Description: The development of highly reactive and stereoselective catalytic systems is required not only to improve existing synthetic methods but also to invent distinct chemical reactions. Herein, a homogenized combination of nickel-based Lewis acid–surfactant-combined catalysts and single-walled carbon nanotubes is shown to exhibit substantial activity in water. In addition to the enhanced reactivity, stereoselective performance and long-term stability were demonstrated in asymmetric conjugate addition reactions of aldoximes to furnish chiral nitrones in high yields with excellent selectivities. The practical and straightforward application of the designed catalysts in water provides an expedient, environmentally benign, and highly efficient pathway to access optically active compounds.
    Keywords: Chemistry
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  • 55
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-11-02
    Keywords: Chemistry
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  • 56
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-12-14
    Keywords: Chemistry
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  • 57
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-10-26
    Keywords: Chemistry
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  • 58
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-11-02
    Description: Exploration of intermediates that enable chemoselective cycloaddition reactions and expeditious construction of fused- or bridged-ring systems is a continuous challenge for organic synthesis. As an intermediate of interest, the oxyallyl cation has been harnessed to synthesize architectures containing seven-membered rings via (4+3) cycloaddition. However, its potential to access five-membered skeletons is underdeveloped, largely due to the thermally forbidden (3+2) pathway. Here, the combination of a tailored precursor and a Pd(0) catalyst generates a Pd-oxyallyl intermediate that cyclizes with conjugated dienes to produce a diverse array of tetrahydrofuran skeletons. The cycloaddition overrides conventional (4+3) selectivity by proceeding through a stepwise pathway involving a Pd-allyl transfer and ring closure sequence. Subsequent treatment of the (3+2) adducts with a palladium catalyst converts the heterocycles to the carbocyclic cyclopentanones.
    Keywords: Chemistry
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  • 59
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-11-16
    Keywords: Chemistry
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  • 60
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-10
    Keywords: Chemistry
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  • 61
    Publication Date: 2018-08-10
    Description: Understanding the practical limitations of chemical reactions is critically important for efficiently planning the synthesis of compounds in pharmaceutical, agrochemical, and specialty chemical research and development. However, literature reports of the scope of new reactions are often cursory and biased toward successful results, severely limiting the ability to predict reaction outcomes for untested substrates. We herein illustrate strategies for carrying out large-scale surveys of chemical reactivity by using a material-sparing nanomole-scale automated synthesis platform with greatly expanded synthetic scope combined with ultrahigh-throughput matrix-assisted laser desorption/ionization–time-of-flight mass spectrometry (MALDI-TOF MS).
    Keywords: Chemistry
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  • 62
    Publication Date: 2018-08-24
    Description: Researchers around the world have observed the formation of molecularly ordered structures of unknown origin on the surface of titanium dioxide (TiO 2 ) photocatalysts exposed to air and solution. Using a combination of atomic-scale microscopy and spectroscopy, we show that TiO 2 selectively adsorbs atmospheric carboxylic acids that are typically present in parts-per-billion concentrations while effectively repelling other adsorbates, such as alcohols, that are present in much higher concentrations. The high affinity of the surface for carboxylic acids is attributed to their bidentate binding. These self-assembled monolayers have the unusual property of being both hydrophobic and highly water-soluble, which may contribute to the self-cleaning properties of TiO 2 . This finding is relevant to TiO 2 photocatalysis, because the self-assembled carboxylate monolayers block the undercoordinated surface cation sites typically implicated in photocatalysis.
    Keywords: Chemistry
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  • 63
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-31
    Keywords: Chemistry
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  • 64
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-08-31
    Keywords: Chemistry
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  • 65
    Publication Date: 2018-08-31
    Description: The alkaline earth metals calcium (Ca), strontium (Sr), and barium (Ba) typically engage in chemical bonding as classical main-group elements through their n s and n p valence orbitals, where n is the principal quantum number. Here we report the isolation and spectroscopic characterization of eight-coordinate carbonyl complexes M(CO) 8 (where M = Ca, Sr, or Ba) in a low-temperature neon matrix. Analysis of the electronic structure of these cubic O h -symmetric complexes reveals that the metal–carbon monoxide (CO) bonds arise mainly from [M(d )] -〉 (CO) 8 backdonation, which explains the strong observed red shift of the C-O stretching frequencies. The corresponding radical cation complexes were also prepared in gas phase and characterized by mass-selected infrared photodissociation spectroscopy, confirming adherence to the 18-electron rule more conventionally associated with transition metal chemistry.
    Keywords: Chemistry
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  • 66
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-09-07
    Keywords: Chemistry
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  • 67
    Publication Date: 2018-09-07
    Description: Mystery surrounds the transition from gas-phase hydrocarbon precursors to terrestrial soot and interstellar dust, which are carbonaceous particles formed under similar conditions. Although polycyclic aromatic hydrocarbons (PAHs) are known precursors to high-temperature carbonaceous-particle formation, the molecular pathways that initiate particle formation are unknown. We present experimental and theoretical evidence for rapid molecular clustering–reaction pathways involving radicals with extended conjugation. These radicals react with other hydrocarbon species to form covalently bound complexes that promote further growth and clustering by regenerating resonance-stabilized radicals through low-barrier hydrogen-abstraction and hydrogen-ejection reactions. Such radical–chain reaction pathways may lead to covalently bound clusters of PAHs and other hydrocarbons that would otherwise be too small to condense at high temperatures, thus providing the key mechanistic steps for rapid particle formation and surface growth by hydrocarbon chemisorption.
    Keywords: Chemistry
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  • 68
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-09-14
    Keywords: Chemistry
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  • 69
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-04-27
    Keywords: Chemistry
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  • 70
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-04-27
    Keywords: Chemistry
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  • 71
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-04-27
    Description: Basic heteroarenes are a ubiquitous feature of pharmaceuticals and bioactive molecules, and Minisci-type additions of radical nucleophiles are a leading method for their elaboration. Despite many Minisci-type protocols that result in the formation of stereocenters, exerting control over the absolute stereochemistry at these centers remains an unmet challenge. We report a process for addition of prochiral radicals, generated from amino acid derivatives, to pyridines and quinolines. Our method offers excellent control of both enantioselectivity and regioselectivity. An enantiopure chiral Brønsted acid catalyst serves both to activate the substrate and induce asymmetry, while an iridium photocatalyst mediates the required electron transfer processes. We anticipate that this method will expedite access to enantioenriched small-molecule building blocks bearing versatile basic heterocycles.
    Keywords: Chemistry
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  • 72
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-05-25
    Keywords: Chemistry
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  • 73
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-05-25
    Keywords: Chemistry
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  • 74
    Publication Date: 2018-10-26
    Description: Primary amines are essential constituents of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains challenging. Here, we report a general strategy to access primary amines from alkenes through an operationally simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative and benign sodium chloride act as the respective nitrogen and chlorine sources. The reaction proceeds at room temperature under air; tolerates a large scope of aliphatic and conjugated alkenes, including densely functionalized substrates; and provides excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity of the 2-chloroalkylamine products, an understudied class of amphoteric molecules, enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido amines, and homoallylic amines.
    Keywords: Chemistry
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  • 75
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-11-09
    Keywords: Chemistry
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  • 76
    Publication Date: 2018-11-09
    Description: Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed.
    Keywords: Chemistry
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  • 77
    Publication Date: 2018-11-16
    Description: Heterobiaryls composed of pyridine and diazine rings are key components of pharmaceuticals and are often central to pharmacological function. We present an alternative approach to metal-catalyzed cross-coupling to make heterobiaryls using contractive phosphorus C–C couplings, also termed phosphorus ligand coupling reactions. The process starts by regioselective phosphorus substitution of the C–H bonds para to nitrogen in two successive heterocycles; ligand coupling is then triggered via acidic alcohol solutions to form the heterobiaryl bond. Mechanistic studies imply that ligand coupling is an asynchronous process involving migration of one heterocycle to the ipso position of the other around a central pentacoordinate P(V) atom. The strategy can be applied to complex drug-like molecules containing multiple reactive sites and polar functional groups, and also enables convergent coupling of drug fragments and late-stage heteroarylation of pharmaceuticals.
    Keywords: Chemistry
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  • 78
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-07-06
    Keywords: Chemistry
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  • 79
    Publication Date: 2018-07-06
    Description: Conical intersections play a critical role in excited-state dynamics of polyatomic molecules because they govern the reaction pathways of many nonadiabatic processes. However, ultrafast probes have lacked sufficient spatial resolution to image wave-packet trajectories through these intersections directly. Here, we present the simultaneous experimental characterization of one-photon and two-photon excitation channels in isolated CF 3 I molecules using ultrafast gas-phase electron diffraction. In the two-photon channel, we have mapped out the real-space trajectories of a coherent nuclear wave packet, which bifurcates onto two potential energy surfaces when passing through a conical intersection. In the one-photon channel, we have resolved excitation of both the umbrella and the breathing vibrational modes in the CF 3 fragment in multiple nuclear dimensions. These findings benchmark and validate ab initio nonadiabatic dynamics calculations.
    Keywords: Chemistry
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  • 80
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-07-13
    Keywords: Chemistry
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  • 81
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-06-22
    Keywords: Chemistry
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  • 82
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-04-13
    Keywords: Chemistry
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  • 83
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-05-04
    Keywords: Chemistry
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  • 84
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-05-11
    Keywords: Chemistry
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  • 85
    Publication Date: 2018-05-11
    Description: Common anionic nucleophiles such as those derived from inorganic salts have not been used for enantioselective catalysis because of their insolubility. Here, we report that merging hydrogen bonding and phase-transfer catalysis provides an effective mode of activation for nucleophiles that are insoluble in organic solvents. This catalytic manifold relies on hydrogen bonding complexation to render nucleophiles soluble and reactive, while simultaneously inducing asymmetry in the ensuing transformation. We demonstrate the concept using a chiral bis-urea catalyst to form a tridentate hydrogen bonding complex with fluoride from its cesium salt, thereby enabling highly efficient enantioselective ring opening of episulfonium ion. This fluorination method is synthetically valuable considering the scarcity of alternative protocols and points the way to wider application of the catalytic approach with diverse anionic nucleophiles.
    Keywords: Chemistry
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  • 86
    Publication Date: 2018-05-18
    Description: Carbon dioxide (CO 2 ) electroreduction could provide a useful source of ethylene, but low conversion efficiency, low production rates, and low catalyst stability limit current systems. Here we report that a copper electrocatalyst at an abrupt reaction interface in an alkaline electrolyte reduces CO 2 to ethylene with 70% faradaic efficiency at a potential of –0.55 volts versus a reversible hydrogen electrode (RHE). Hydroxide ions on or near the copper surface lower the CO 2 reduction and carbon monoxide (CO)–CO coupling activation energy barriers; as a result, onset of ethylene evolution at –0.165 volts versus an RHE in 10 molar potassium hydroxide occurs almost simultaneously with CO production. Operational stability was enhanced via the introduction of a polymer-based gas diffusion layer that sandwiches the reaction interface between separate hydrophobic and conductive supports, providing constant ethylene selectivity for an initial 150 operating hours.
    Keywords: Chemistry
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  • 87
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-05-25
    Keywords: Chemistry
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  • 88
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-03-23
    Description: White phosphorus, generated in the legacy thermal process for phosphate rock upgrading, has long been the key industrial intermediate for the synthesis of phosphorus-containing chemicals, including herbicides, flame-retardants, catalyst ligands, battery electrolytes, pharmaceuticals, and detergents. In contrast, phosphate fertilizers are made on a much larger scale from phosphoric acid, obtained by treating phosphate rock with sulfuric acid. Dehydration of phosphoric acid using sodium chloride gives trimetaphosphate, and here we report that trichlorosilane, primarily used for the production of high-purity silicon, reduces trimetaphosphate to the previously unknown bis(trichlorosilyl)phosphide anion. This anion offers an entry point to value-added organophosphorus chemicals such as primary and secondary alkyl phosphines, and thus to organophosphinates, and can also be used to prepare phosphine gas and the hexafluorophosphate anion, all previously available only downstream from white phosphorus.
    Keywords: Chemistry
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  • 89
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-04-06
    Keywords: Chemistry
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  • 90
    Publication Date: 2018-04-06
    Description: Cross-coupling chemistry is widely applied to carbon-carbon bond formation in the synthesis of medicines, agrochemicals, and other functional materials. Recently, single-electron–induced variants of this reaction class have proven particularly useful in the formation of C(sp 2 )–C(sp 3 ) linkages, although certain compound classes have remained a challenge. Here, we report the use of sulfones to activate the alkyl coupling partner in nickel-catalyzed radical cross-coupling with aryl zinc reagents. This method’s tolerance of fluoroalkyl substituents proved particularly advantageous for the streamlined preparation of pharmaceutically oriented fluorinated scaffolds that previously required multiple steps, toxic reagents, and nonmodular retrosynthetic blueprints. Five specific sulfone reagents facilitate the rapid assembly of a vast set of compounds, many of which contain challenging fluorination patterns.
    Keywords: Chemistry
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  • 91
    Publication Date: 2018-05-04
    Description: Plasmon-induced chemical reactions of molecules adsorbed on metal nanostructures are attracting increased attention for photocatalytic reactions. However, the mechanism remains controversial because of the difficulty of direct observation of the chemical reactions in the plasmonic field, which is strongly localized near the metal surface. We used a scanning tunneling microscope (STM) to achieve real-space and real-time observation of a plasmon-induced chemical reaction at the single-molecule level. A single dimethyl disulfide molecule on silver and copper surfaces was dissociated by the optically excited plasmon at the STM junction. The STM study combined with theoretical calculations shows that this plasmon-induced chemical reaction occurred by a direct intramolecular excitation mechanism.
    Keywords: Chemistry
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  • 92
    Publication Date: 2018-05-25
    Description: Identifying catalyst activation modes that exploit one-electron chemistry and overcome associated deactivation pathways will be transformative for developing first-row transition metal catalysts with performance equal or, ideally, superior to precious metals. Here we describe a zinc-activation method compatible with high-throughput reaction discovery that identified scores of cobalt-phosphine combinations for the asymmetric hydrogenation of functionalized alkenes. An optimized catalyst prepared from ( R , R )-Ph-BPE {Ph-BPE, 1,2-bis[(2 R ,5 R )-2,5-diphenylphospholano]ethane} and cobalt chloride [CoCl 2 ·6H 2 O] exhibited high activity and enantioselectivity in protic media and enabled the asymmetric synthesis of the epilepsy medication levetiracetam at 200-gram scale with 0.08 mole % catalyst loading. Stoichiometric studies established that the cobalt (II) catalyst precursor ( R , R )-Ph-BPECoCl 2 underwent ligand displacement by methanol, and zinc promoted facile one-electron reduction to cobalt (I), which more stably bound the phosphine.
    Keywords: Chemistry
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  • 93
    Publication Date: 2018-06-01
    Description: Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.
    Keywords: Chemistry
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  • 94
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-05-18
    Keywords: Chemistry
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  • 95
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-06-01
    Keywords: Chemistry
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  • 96
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-03-23
    Keywords: Chemistry
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  • 97
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-03-23
    Keywords: Chemistry
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  • 98
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    American Association for the Advancement of Science (AAAS)
    In: Science
    Publication Date: 2018-03-30
    Keywords: Chemistry
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  • 99
    Publication Date: 2018-03-30
    Description: The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Brønsted acidic sites of appropriate strength can protonate olefins and thereby generate carbocations that ultimately react to form natural products. Although chemists have recently designed chiral Brønsted acid catalysts to activate imines and carbonyl compounds, mimicking these enzymes to protonate simple olefins that then engage in asymmetric catalytic reactions has remained a substantial synthetic challenge. Here, we show that a class of confined and strong chiral Brønsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. The methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (–)-Boivinianin A.
    Keywords: Chemistry
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  • 100
    Publication Date: 2018-04-13
    Description: Machine learning methods are becoming integral to scientific inquiry in numerous disciplines. We demonstrated that machine learning can be used to predict the performance of a synthetic reaction in multidimensional chemical space using data obtained via high-throughput experimentation. We created scripts to compute and extract atomic, molecular, and vibrational descriptors for the components of a palladium-catalyzed Buchwald-Hartwig cross-coupling of aryl halides with 4-methylaniline in the presence of various potentially inhibitory additives. Using these descriptors as inputs and reaction yield as output, we showed that a random forest algorithm provides significantly improved predictive performance over linear regression analysis. The random forest model was also successfully applied to sparse training sets and out-of-sample prediction, suggesting its value in facilitating adoption of synthetic methodology.
    Keywords: Chemistry
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