Visible-Light Photocatalytic Synthesis of Difluoromethylated Selenides from Selenosulfonates through a Radical Process

J Org Chem. 2023 Sep 1;88(17):12658-12667. doi: 10.1021/acs.joc.3c01352. Epub 2023 Aug 18.

Abstract

A photocatalytic synthesis of difluoromethylated selenides from selenosulfonates is described here. Bench-stable difluoromethyl phosphonium salt [Ph3PCF2H]Br reacts smoothly with selenosulfonates to give a series of functionalized difluoromethylated selenides in moderate to good yields via a radical process. This protocol is free of a stoichiometric base and reductant, has tolerance of functional groups, and has successful late-stage modification of bioactive molecules, which provides facile access to molecules of pharmaceutical relevance.