Volume 136, Issue 14 e202400839
Zuschrift

Controllable Double Difluoromethylene Insertions into S−Cu Bonds: (Arylthio)tetrafluoroethylation of Aryl Iodides with TMSCF2Br

Dr. Shitao Pan

Dr. Shitao Pan

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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Dr. Qiqiang Xie

Dr. Qiqiang Xie

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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Dr. Xiu Wang

Dr. Xiu Wang

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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Rumin Huang

Rumin Huang

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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Yuhao Lu

Yuhao Lu

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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Dr. Chuanfa Ni

Dr. Chuanfa Ni

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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Prof. Dr. Jinbo Hu

Corresponding Author

Prof. Dr. Jinbo Hu

Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China

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First published: 15 February 2024

Abstract

A new method of constructing “ArSCF2CF2Cu” from ArSCu and TMSCF2Br (TMS=trimethylsilyl) has been developed. The cross-coupling reactions of the obtained “ArSCF2CF2Cu” with diverse aryl iodides (Ar′I) provide an efficient access to Ar′CF2CF2SAr. Mechanistic studies demonstrate that the “ArSCF2CF2Cu” species were generated through controllable double difluoromethylene insertions into ArS−Cu bonds rather than the 1,2-addition of ArSCu to tetrafluoroethylene.

Data Availability Statement

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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