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Rhodium‐Catalyzed [2+2+1+1] Cyclocarbonylative Coupling of Alkynes with Carbon Monoxide Affording Tetrasubstituted p ‐Benzoquinones
Author(s) -
Huang Qiufeng,
Hua Ruimao
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700839
Subject(s) - carbon monoxide , catalysis , chemistry , rhodium , coupling reaction , reaction conditions , coupling (piping) , carboxylate , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
Abstract In this strategy, the tetrasubstituted benzoquinones have been prepared directly by a [2+2+1+1] cyclocarbonylative coupling reaction of internal alkynes with CO in the presence of [RhCl(CO) 2 ] 2 . The low concentration of CO in the reaction is the crucial point for the chemoselective formation of tetrasubstituted benzoquinones in good to high yields. Functional groups such as chloro, methoxy, cyano, vinyl, fluoro, and carboxylate are tolerated under the reaction conditions.