Deprotonation of a Borohydride: Synthesis of a Carbene-Stabilized Boryl Anion

Authors

  • David A. Ruiz,

    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • Gaël Ung,

    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • Dr. Mohand Melaimi,

    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • Prof. Guy Bertrand

    Corresponding author
    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
    • UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • The authors gratefully acknowledge financial support from the NIH (R01 GM 68825) and DOE (DE-SC0009376), and Dr. C. Moore for assistance with X-ray crystallography.

Abstract

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An acidic hydride! Thanks to the presence of a π-acceptor cyclic alkyl amino carbene and of two electron-withdrawing nitrile groups, a borohydride reacts with a base to give a carbene-stabilized boryl anion, which reacts with carbon and metal electrophiles at the boron center. Dipp=2,6-diisopropylphenyl, KHMDS=potassium bis(trimethylsilyl)amide.

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