Iron(II)-Catalyzed Trifluoromethylation of Potassium Vinyltrifluoroborates

Authors

  • Dr. Andrew T. Parsons,

    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • Todd D. Senecal,

    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. (F32M093532). The Varian 300 MHz and Bruker 400 MHz NMR spectrometers used in this work were supported by grants from the National Science Foundation (CHE-9808061 and DBI-9729592) and National Institutes of Health (1S10RR13886-01), respectively.

Abstract

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Exchanging BF3 by CF3: The title reaction proceeds under exceedingly mild reaction conditions and provides 2-arylvinyl- and 2-heteroarylvinyl-substituted substrates with E/Z selectivities of more than 95:5. Experimental observations suggest that the reaction does not proceed through a transmetalation of the RBF3K species to the iron catalyst.

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