Triethyl amine as an effective reducing agent for sulfoxide deoxygenation

Org Biomol Chem. 2024 Apr 24;22(16):3215-3219. doi: 10.1039/d4ob00219a.

Abstract

Enabled by triethyl amine (Et3N) and thionyl chloride (SOCl2), an efficient and practical protocol for deoxygenation of sulfoxide to sulfide was developed. This new method features a wide range of substrate scope, including diaryl, dialkyl and aryl alkyl substituted sulfoxides. Detailed mechanistic investigations reveal the crucial role played by Et3N as an electron-donating reductant rather than a hydrogen-atom donor.