Photoinduced C(sp³)–H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer

Abstract

A photoinduced, iron(III) chloride-catalyzed C-H activation of <i>N</i>-methyl amides and ethers leads to the formation of C-S and C-Se bonds via a ligand-to-metal charge transfer (LMCT) process. This methodology converts secondary and tertiary amides, sulfonamides, and carbamates into the corresponding amido-<i>N,S</i>-acetal derivatives in good yields. Mechanistic work revealed that this transformation proceeds through a hydrogen atom transfer (HAT) involving chlorine radical intermediates.