Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents.

Abstract

A protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fashion. Mechanistic studies suggest that the reaction proceeds via generation of an alkyl radical from the alkyl aldehyde, addition of the radical to the furan ring, and subsequent rearomatization.