Publication Date:
2015-05-23
Description:
The synthesis and functionalization of amines are fundamentally important in a vast range of chemical contexts. We present an amine synthesis that repurposes two simple feedstock building blocks: olefins and nitro(hetero)arenes. Using readily available reactants in an operationally simple procedure, the protocol smoothly yields secondary amines in a formal olefin hydroamination. Because of the presumed radical nature of the process, hindered amines can easily be accessed in a highly chemoselective transformation. A screen of more than 100 substrate combinations showcases tolerance of numerous unprotected functional groups such as alcohols, amines, and even boronic acids. This process is orthogonal to other aryl amine syntheses, such as the Buchwald-Hartwig, Ullmann, and classical amine-carbonyl reductive aminations, as it tolerates aryl halides and carbonyl compounds.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Gui, Jinghan -- Pan, Chung-Mao -- Jin, Ying -- Qin, Tian -- Lo, Julian C -- Lee, Bryan J -- Spergel, Steven H -- Mertzman, Michael E -- Pitts, William J -- La Cruz, Thomas E -- Schmidt, Michael A -- Darvatkar, Nitin -- Natarajan, Swaminathan R -- Baran, Phil S -- GM-097444/GM/NIGMS NIH HHS/ -- New York, N.Y. -- Science. 2015 May 22;348(6237):886-91. doi: 10.1126/science.aab0245. Epub 2015 May 21.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA. ; Discovery Chemistry, Bristol-Myers Squibb, Princeton, NJ 08543, USA. ; Chemical Development, Bristol-Myers Squibb, New Brunswick, NJ 08903, USA. ; Kemxtree LLC, 1370 Hamilton Street, Somerset, NJ 08873, USA. ; Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA. pbaran@scripps.edu.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/25999503" target="_blank"〉PubMed〈/a〉
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
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Chemistry and Pharmacology
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Computer Science
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Medicine
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Natural Sciences in General
,
Physics
