The Synthesis of (E)‐Vinyl and Alkynyl Sulfones by the Formation of an Electron Donor‐Acceptor Complex Using Thiosulfonates and Sodium Iodide Under Visible Light

Author:

Cao Kun1,Zhang Naiyou1,Lin Li1,Shen Qing2,Jiang Hezhong1,Li Jiahong1ORCID

Affiliation:

1. School of Life Science and Engineering Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs Southwest Jiaotong University. Chengdu 610031 People's Republic of China

2. Department of Pharmacy Personalized Drug Therapy Key Laboratory of Sichaun Province Sichaun Academy of Medical Science & Sichuan Provincial People's Hospital School of Medicine University of Electronic Science and Technology of China Chengdu 610072 People's Republic of China

Abstract

AbstractA method for the synthesis of (E)‐vinyl sulfones and alkynyl sulfones through the cleavage of thiosulfonate promoted by the formation of EDA complexes under visible light irradiation at room temperature without the need for other metal catalysts is described. The mechanism study shows that sodium iodide and thiosulfonate form EDA complexes under visible light irradiation, resulting in a single‐electron transfer cleavage to generate sulfonyl radicals, which then react with olefins or alkynes to produce (E)‐vinyl sulfones or alkynyl sulfones, respectively. This method is applicable to 44 olefin and alkyne substrates, with yields ranging from 38% to 90%, providing a radical synthesis approach for the preparation of sulfonylated compounds.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry

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