Deprotonation of a borohydride: synthesis of a carbene-stabilized boryl anion

Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7590-2. doi: 10.1002/anie.201303457. Epub 2013 Jun 13.

Abstract

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.

Keywords: anions; boron; gold; nucleophiles.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anions / chemistry
  • Borohydrides / chemical synthesis
  • Borohydrides / chemistry*
  • Crystallography, X-Ray
  • Gold / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Conformation
  • Protons

Substances

  • Anions
  • Borohydrides
  • Protons
  • carbene
  • Gold
  • Methane