A metal-free approach for the synthesis of thiosulfonates from sulfonyl hydrazides

Without any metal catalyst, an efficient transformation of a variety of sulfonyl hydrazides into the corresponding thiosulfonates mediated by NBS/DABCO under air is developed. The method utilizes mild reaction conditions, affords moderate to good yields of product, and tolerates a broad substrate scope. A plausible mechanism is proposed for the decomposition of the sulfonyl hydrazides and the construction of S(O-2)-S bonds to form thiosulfonates.

Automated summary

This study presents an efficient transformation of sulfonyl hydrazides into thiosulfonates using NBS/DABCO without the need for any metal catalyst. The method offers mild reaction conditions, moderate to good yields, and a broad substrate scope. A plausible mechanism for the reaction is proposed involving the decomposition of sulfonyl hydrazides and the formation of S(O-2)-S bonds to produce thiosulfonates.