TBAI-catalyzed ring-opening sulfonylations of benzothiazoles and arylsulfonyl hydrazides

Abstract

An efficient TBAI-catalyzed ring-opening sulfonylation of benzo[d]thiazole and arylsulfonyl hydrazide has been developed. Various benzo[d]thiazole as good thiol surrogates are compatible with the catalytic conditions, providing diversified unsymmetrical thiosulfonates with good yields. This strategy features mild reaction conditions, broad substrate scope, readily available starting materials, and gram-scale synthesis. Importantly, these products can be readily converted to novel o-amino-substituted diaryl sulfides.

Keywords

• Benzothiazoles
• Ring-opening
• Sulfonylation
• Arylsulfonyl hydrazide
• Thiosulfonate