Photoexcited Hantzsch Ester Anions Enabled C-F Bond Activation and Hydro-difluoroalkylation of Arylethylenes Through Dual-SET Process

Chemistry. 2024 Dec 23:e202404116. doi: 10.1002/chem.202404116. Online ahead of print.

Abstract

In this study, we reported a new approach to activate the C-F bond of trifluoromethylarenes to achieve the hydro-difluoroalkylation of arylethylenes using photoexcited Hantzsch esters (HEs) anions. A wide range of α,α-difluoroalkanes was synthesized. Late-stage functionalization of drug molecules and synthesis of bioactive molecule bioisostere were also presented. Mechanistic studies revealed that the dual-single electron transfer (SET) process of HEs anion was the key to this reaction.

Keywords: C-F bond functionalization; Dual-SET Process; Hantzsch esters (HEs) anions; Hydro-difluoroalkylation of arylethylenes; Photoreduction.