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

Xuqiang Guo; Xuejun Sun; Mengmeng Jiang; Yulei Zhao

doi:10.1055/a-1701-6700

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(08): 1996-2004
DOI: 10.1055/a-1701-6700

paper

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

Xuqiang Guo‡

,

Xuejun Sun‡

,

Mengmeng Jiang

,

Yulei Zhao ∗

Abstract

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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

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Referenzen

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