Direct S-Azidomethylation of Thiols with N-Azidomethyldisulfonimides

Abstract

A direct azidomethylation reaction at the sulfur atoms of thiols with N-azidomethyldisulfonimides is presented, providing a facile and efficient approach for the synthesis of azidomethylated compounds with broad substrate scope and mild reaction conditions. Under optimized conditions using N-azidomethyl-bis(4-trifluoromethylbenzene)sulfonimide as the azidomethyl source, various aliphatic and aromatic thiols furnish the corresponding S-azidomethyl compounds in moderate to high yields. The reaction proceeds selectively at the mercapto group, even in substrates bearing polar functional groups.