Visible‐Light‐Induced Selective Photolysis of Phosphonium Iodide Salts for Monofluoromethylations

Abstract

AbstractThe sigma (σ)‐hole effect has emerged as a promising tool to construct novel architectures endowed with new properties. A simple yet effective strategy for the generation of monofluoromethyl radicals is a continuing challenge within the synthetic community. Fluoromethylphosphonium salts are easily available, air‐ and thermally stable, as well as simple‐to‐handle. Herein, we report the ability of the σ‐hole effect to facilitate the visible‐light‐triggered photolysis of phosphonium iodide salts, a charge‐transfer complex, selectively giving fluoromethyl radicals. The usefulness and versatility of this new protocol are demonstrated through the mono‐, di‐, and trifluoromethylation of a variety of alkenes.