Polarity-Driven Thiyl Radical-Catalyzed Aerobic Debenzylation of Ethers and Amines

Abstract

We report the use of a strongly electrophilic thiyl radical derived from commercially available pentafluorothiophenol as a demonstration of highly chemoselective H atom abstraction from electron-rich and relatively weak benzylic C-H bonds adjacent to the O and N atoms. This approach enables the selective oxidative removal of benzyl and p-methoxybenzyl groups from amines and ethers under ambient aerobic conditions.