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Synthesis of Biaryl Compounds by Vinylogous Michael Reactions
Author(s) -
Christoffers Jens,
Mann Alexander
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:10<1977::aid-ejoc1977>3.0.co;2-z
Subject(s) - chemistry , michael reaction , cycloaddition , aldol reaction , enone , quinone , tautomer , acceptor , organic chemistry , stereochemistry , catalysis , physics , condensed matter physics
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 .