Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO2 center dot CH2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.

Automated summary

This method has been developed to convert structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite, featuring transition-metal-free conditions, operational simplicity, and readily available reagents. It is the first example of using a reductant to assist in the synthesis of thiosulfonates. Mechanistic studies suggest that this transformation likely proceeds via a reducing-coupling pathway.