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Synthesis of Biaryl Compounds by Vinylogous Michael Reactions (2000)

Christoffers, Jens ; Mann, Alexander

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1977-1982

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ISSN: 1434-193X

Keywords: Biaryls ; Homogeneous catalysis ; Iron ; Addition reactions ; Quinones ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---Acceptor-substituted cycloalkenones 1 undergo an iron(III)-catalyzed vinylogous Michael reaction - a sequence of enone-dienol tautomerism, [4+2]-cycloaddition, and retro-aldol reaction - with quinone derivatives 3. A variety of products is obtained ranging from meta-terphenyl precursors 5 to dihydronaphthobenzofurans 7. Reaction of 1,2-naphthoquinone (3e) with vinylogous donors 1 yields cross-coupled products 12, which can be further converted into highly functionalized biaryl compounds 13 and 14.

Type of Medium: Electronic Resource

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