Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene

[摘要] This report describes the scope and mechanism of the solvent-dependent, chemoselective oxidative coupling of 1-aryl-1,3-dicarbonyls with styrene using Ce(IV) reagents. Dihydrofuran derivatives are obtained when reactions are performed in methanol whereas alpha-tetralones can be selectively synthesized in acetonitrile and methylene chloride. Mechanistic studies are consistent with the rate of solvent-assisted deprotonation of a radical cation intermediate playing an integral role in the selective formation of products. (c) 2009 Elsevier Ltd. All rights reserved.

[发布日期] 2009-12-26