Hypervalent Iodine Mediated Synthesis of Thiosulfonates from Sulfonyl Hydrazides and Their Transformation into Symmetrical Disulfides

Abstract

A transition-metal-free synthesis of thiosulfonates has been accomplished by the disproportionate coupling of readily available and inexpensive sulfonyl hydrazides embracing hypervalent iodine(III) [phenyliodine(III) diacetate (PIDA)] as an oxidant. This synthesis involves cleavage of the S–N bond and is endowed with creation of a new S–S bond. The thiosulfonates were further reduced with CS₂/KOH to obtain symmetrical disulfides. This protocol features mild reaction conditions in open air, an inexpensive oxidant, and high functional group tolerance with good to excellent product yields.

Key words

thiosulfonates - hypervalent iodine - sulfonyl hydrazides - reduction - symmetrical disulfides

Publication History

Received: 19 December 2023

Accepted after revision: 02 February 2024

Accepted Manuscript online:
02 February 2024

Article published online:
22 February 2024

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