Synthesis of gem-Difluorinated Cyclopropanes and Cyclopropenes: Trifluoromethyltrimethylsilane as a Difluorocarbene Source

Authors

  • Fei Wang,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China), Fax: (+86) 21-6416-6128
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  • Tao Luo,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China), Fax: (+86) 21-6416-6128
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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), Fax: (+86) 21-6416-6128
    • Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China), Fax: (+86) 21-6416-6128
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  • Dr. Ying Wang,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
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  • Hema S. Krishnan,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
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  • Dr. Parag V. Jog,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
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  • Dr. Somesh K. Ganesh,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
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  • Prof. Dr. G. K. Surya Prakash,

    Corresponding author
    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
    • Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
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  • Prof. Dr. George A. Olah

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661 (USA), Fax: (+1) 213-740-6679
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  • Support of our work by the National Natural Science Foundation of China (20772144, 20825209, 20832008) and financial support by the Loker Hydrocarbon Research Institute is gratefully acknowledged.

Abstract

original image

Highly versatile: The Ruppert–Prakash reagent (Me3SiCF3) can be an efficient source of difluorocarbene. By varying the nonmetallic initiator that is used (F at lower temperatures and I at higher temperatures), a range of structurally diverse alkenes and alkynes can be converted into the corresponding gem-difluorinated cyclopropanes and cyclopropenes in good yields (see scheme).

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