Iron-Catalyzed Photochemical Synthesis of Sulfinamides from Aliphatic Hydrocarbons and Sulfinylamines

Abstract

An iron-catalyzed photochemical sulfinamidation of hydrocarbons with N-sulfinylamines has been developed. The merger of ligand-to-metal charge transfer (LMCT) of FeCl 3 with hydrogen atom transfer (HAT) process is the key for the generation of alkyl radicals from hydrocarbons, and the resultant alkyl radicals were readily trapped by N-sulfinylamines to produce structurally diverse sulfinamides. Contrary to traditional methods that inevitably use sensitive organometallic reagents and prefunctionalized substrates, our approach features simple operation and the wide availability of starting materials. Gratifyingly, the reaction is scalable, and the obtained sulfinamides can be conveniently converted to highly functionalized sulfur(VI) derivatives.