Copper-Catalyzed Trifluoromethylation of Unactivated Olefins

Authors

  • Dr. Andrew T. Parsons,

    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • Prof. Dr. Stephen L. Buchwald

    Corresponding author
    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
    • Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • We thank the National Institutes of Health (GM46059) for financial support of this project and for a postdoctoral fellowship to A.T.P. (F32GM093532). The Varian 300 MHz and Bruker 400 MHz NMR spectrometers used in this work were supported by grants from the National Science Foundation (ACHE-9808061 and DBI-9729592) and the National Institutes of Health (1S10RR13886-01), respectively.

Abstract

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Activating the inactive: A copper-catalyzed allylic trifluoromethylation of unactivated terminal olefins proceeds under mild conditions to produce linear allylic trifluoromethylated products with high E/Z selectivity (see scheme). The reaction can be applied to a range of substrates bearing numerous functional groups. Furthermore, the reaction is scalable and amenable to a benchtop setup.

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