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

Synthesis DOI: 10.1055/a-2260-0346 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. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - February 22, 2024 Category: Chemistry Authors: Yadav, Ashvani Kumar, Rohit Prasad, Virendra Tags: paper Source Type: research