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

Autor: Julien Monot, Louis Fensterbank, Max Malacria, Emmanuel Lacôte, Steven J. Geib, Dennis P. Curran
Jazyk: angličtina
Rok vydání: 2010
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 6, Iss 1, Pp 709-712 (2010)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.6.82
Popis: 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 and X-ray crystallography. In contrast, a CAAC complex with borane (BH3) 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.
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