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CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF? and BH?.

ABSTRACT: In situ formation of two cyclic (alkyl) (amino) carbenes (CAACs) followed by addition of BF?•Et?O provided the first two examples of CAAC-BF? complexes: 1-(2,6-diisopropylphenyl)-3,5,5-trimethyl-3-phenylpyrrolidin-2-ylidene trifluoroborane, and 2-(2,6-diisopropylphenyl)-3,3-dimethyl-2-azaspiro[4.5]decan-1-ylidene trifluoroborane. These CAAC-BF? complexes are robust compounds that are stable to ambient laboratory conditions and silica gel chromatography. They were characterized by spectroscopy and X-ray crystallography. In contrast, a CAAC complex with borane (BH?) was readily formed in situ according to ¹H and ¹¹B NMR analysis, but did not survive the workup conditions. These results set the stage for further studies of the chemistry of CAAC boranes.

SUBMITTER: Monot J

PROVIDER: S-EPMC2956467 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃.

Monot Julien J Fensterbank Louis L Malacria Max M Lacôte Emmanuel E Geib Steven J SJ Curran Dennis P DP

Beilstein journal of organic chemistry 20100802

In situ formation of two cyclic (alkyl) (amino) carbenes (CAACs) followed by addition of BF₃•Et₂O provided the first two examples of CAAC-BF₃ complexes: 1-(2,6-diisopropylphenyl)-3,5,5-trimethyl-3-phenylpyrrolidin-2-ylidene trifluoroborane, and 2-(2,6-diisopropylphenyl)-3,3-dimethyl-2-azaspiro[4.5]decan-1-ylidene trifluoroborane. These CAAC-BF₃ complexes are robust compounds that are stable to ambient laboratory conditions and silica gel chromatography. They were characterized by spectroscopy an ...[more]

PMID: 20978616

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