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

ABSTRACT: An acidic hydride! Thanks to the presence of a ?-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.

SUBMITTER: Ruiz DA

PROVIDER: S-EPMC3712875 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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

Ruiz David A DA Ung Gaël G Melaimi Mohand M Bertrand Guy G

Angewandte Chemie (International ed. in English) 20130613 29

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. ...[more]

PMID: 23765789

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