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
We thank the Natural Science Foundation of Shandong Province (ZR2018MB014 and ZR2018BB026), College Students Innovation and Entrepreneurship Training Project of China (202110446051), and the Doctoral Start-Up Scientific Research Foundation of Qufu Normal University.


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.

Supporting Information



Publikationsverlauf

Eingereicht: 16. Oktober 2021

Angenommen nach Revision: 19. November 2021

Accepted Manuscript online:
19. November 2021

Artikel online veröffentlicht:
13. Januar 2022

© 2021. Thieme. All rights reserved

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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