Switchable Synthesis of Sulfoxides, Sulfones and Thiosulfonates through Selectfluor-Promoted Oxidation with H₂O as O-Source

Abstract

A practical and efficient protocol for the switchable synthesis of sulfoxides, sulfones, and thiosulfonates via Selectfluor-mediated oxidation of sulfides and thiols, respectively, at ambient temperature has been developed. All these organosulfur compounds can be prepared with nearly quantitative yields by applying eco-friendly H₂O as O-source. The formation of sulfoxides and thiosulfonates takes only a few minutes (3–20 min). As suggested by the control experiments, the oxidation procedure might proceed through the fluorination of sulfide, nucleophilic addition with H₂O, and elimination of hydrogen fluoride.

Key words

oxidation - sulfoxides - sulfones - thiosulfonates - Selectfluor

Publication History

Received: 16 October 2021

Accepted after revision: 19 November 2021

Accepted Manuscript online:
19 November 2021

Article published online:
13 January 2022

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