Cornerstones in Chemistry
Chen's Reagent: A Versatile Reagent for Trifluoromethylation, Difluoromethylenation, and Difluoroalkylation in Organic Synthesis†
Qiqiang Xie,
Jinbo Hu,
Qiqiang Xie
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Jinbo Hu
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China
E-mail: [email protected]Search for more papers by this authorQiqiang Xie,
Jinbo Hu,
Qiqiang Xie
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Jinbo Hu
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 China
E-mail: [email protected]Search for more papers by this authorDedicated to Professor Qing-Yun Chen on the occasion of his 90th birthday.
Summary
Methyl fluorosulfonyldifluoroacetate (FSO2CF2CO2Me or MFSDA), often called “Chen's reagent”, is commonly used to synthesize trifluoromethylated and difluoroalkylated compounds. This important reagent was initially developed as an efficient trifluoromethylating agent by Professor Qing-Yun Chen and co-workers at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences in 1989. Since then, this reagent has been widely used in academia and industry for the copper-mediated trifluoromethylation of aryl, alkenyl, and even some alkyl halides, among others. During the last decade, this reagent was further developed as a difluorocarbene precursor as well as a radical difluoroalkylating agent under visible light promoted redox catalysis. This review aims to briefly highlight the initial discovery, historical development, and synthetic applications of Chen's reagent, and provide some guidelines for readers to use Chen's reagent in their own synthesis.
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- 55The prices of Chen's reagent and TMSCF3 were obtained in November 2019 by searching in the following website: https://www.sigmaaldrich.com/united-states.html.
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