Regioselective direct sulfenylation of glycals using arylsulfonyl chlorides in the presence of triphenylphosphine: access to C2-thioaryl glycosides

Abstract

Direct triphenylphosphine-mediated regioselective sulfenylation of glycals by using various cheap and easily available aryl sulfonyl chlorides as a sulfur source to generate different C2-S-aryl-glycosides was developed. Notably, the features of this protocol offer a milder and easier operational procedure, and broad substrate scope with complete regioselectivity at C-2. Experiments and DFT calculations supported the proposed mechanism and regioselectivity for the formation of C2-S-aryl-glycosides.