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Synthesis of gem-Difluorocyclopropa(e)nes and O-, S-, N-, and P-Difluoromethylated Compounds with TMSCF2Br

Authors

  • Lingchun Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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    • These authors contributed equally to this work.

  • Dr. Fei Wang,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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    • These authors contributed equally to this work.

  • Dr. Chuanfa Ni,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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  • Prof. Dr. Jinbo Hu

    Corresponding author
    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
    • Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)

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  • Support of our work by the National Basic Research Program of China (2012CB215500 and 2012CB821600), the National Natural Science Foundation of China (20825209 and 21202189), and the Chinese Academy of Sciences is gratefully acknowledged. TMS=trimethylsilyl.

Abstract

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Zwei Reaktionswege: Me3SiCF2Br, eine effiziente Quelle für Difluorcarben, ist kompatibel mit neutralem und basischem wässrigem Milieu. Die durch Bromidionen ausgelöste [2+1]-Cycloaddition mit Alkenen/Alkinen und die durch Hydroxidionen vermittelte α-Addition an (Thio)Phenole, (Thio)Alkohole, Sulfinate, heterocyclische Amine und H-Phosphinoxide ergeben gem-difluorierte Produkte mit Toleranz für viele funktionelle Gruppen.

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