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

ABSTRACT: 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.

SUBMITTER: Casey BM 

PROVIDER: S-EPMC2898135 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature