Synthesis 2023; 55(08): 1253-1259
DOI: 10.1055/a-2004-1006
paper

Facile Synthesis of Diaryl Sulfones through Arylsulfonylation of Arynes and Thiosulfonates

Authors

  • Yating Zheng

    a   School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
    b   Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
  • Delin Tang

    a   School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
    b   Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
  • Pei Xie

    a   School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
    b   Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
  • Jinyun Luo

    a   School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
    b   Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
  • Zhihua Cai

    a   School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
    b   Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
  • Lin He

    a   School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
    b   Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

This work was supported by the National Natural Science Foundation of China (No. 22161039) and Shihezi University (Start-up Fund for High-Level Talents, No. KX015001 and International Cooperation Project, No. KX01480304).


Graphical Abstract

Preview

Abstract

A mild and transition-metal-free arylsulfonylation reaction of arynes has been developed. Arynes generated in situ from 2-(trimethylsilyl)aryl triflates undergo nucleophilic addition with thiosulfonates to produce diaryl sulfones in 41–99% yield. The reaction can be scaled easily to gram-scale with the high yield maintained. Finally, mechanistic experiments showed that acetonitrile acted as a proton source.

Supporting Information



Publication History

Received: 11 August 2022

Accepted after revision: 26 December 2022

Accepted Manuscript online:
26 December 2022

Article published online:
13 January 2023

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany