Visible-Light-Induced Difunctionalization of 3-Butenoic Acid with Bromodifluoromethyl Heteroarylsulfones

Org Lett. 2024 Aug 2;26(30):6449-6453. doi: 10.1021/acs.orglett.4c02277. Epub 2024 Jul 22.

Abstract

Herein, we report a visible-light-induced iridium-promoted direct bifunctionalization of 3-butenoic acid with bromodifluoromethyl heteroarylsulfones. This methodology enables the concurrent introduction of difluoromethyl heteroarylsulfone and bromine groups into 3-butenoic acid under mild reaction conditions. Various α-substituted 3-butenoic acids and bromodifluoromethyl heteroarylsulfones were found to be compatible, yielding the corresponding products in moderate to good yields. This method opens a new route for the synthesis of fluorocarboxylic acid derivatives.