title: Deprotonation of a borohydride: synthesis of a carbene-stabilized boryl anion.
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.
authors.affiliation: UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343, USA.
authors.forename: David A
authors.initials: DA
authors.lastname: Ruiz
authors.forename: Gaël
authors.initials: G
authors.lastname: Ung
authors.forename: Mohand
authors.initials: M
authors.lastname: Melaimi
authors.forename: Guy
authors.initials: G
authors.lastname: Bertrand
mesh_terms: D000838:Anions / Q000737:chemistry; D001894:Borohydrides / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006046:Gold / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D011522:Protons
chemical_list: D000838:Anions; D001894:Borohydrides; D011522:Protons; C030011:carbene; D006046:Gold; D008697:Methane
keywords: anions; boron; gold; nucleophiles