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

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.

Automated summary

An efficient ring-opening sulfonylation reaction of benzo[d]thiazole and arylsulfonyl hydrazide catalyzed by TBAI has been developed, allowing for the use of various benzo[d]thiazole as good thiol surrogates to provide diversified products under mild reaction conditions.