期刊
NATURE CHEMISTRY
卷 6, 期 11, 页码 983-988出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2063
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资金
- Natural Sciences and Engineering Research Council of Canada
- Academy of Finland
Perfluorarylborane Lewis acids catalyse the addition of silicon-hydrogen bonds across C=C, C=N and C=O double bonds. This 'metal-free' hydrosilylation has been proposed to occur via borane activation of the silane Si-H bond, rather than through classical Lewis acid/base adducts with the substrate. However, the key borane/silane adduct had not been observed experimentally. Here it is shown that the strongly Lewis acidic, antiaromatic 1,2,3-tris(pentafluorophenyl)-4,5,6,7-tetrafluoro-1-boraindene forms an observable, isolable adduct with triethylsilane. The equilibrium for adduct formation was studied quantitatively through variable-temperature NMR spectroscopic investigations. The interaction of the silane with the borane occurs through the Si-H bond, as evidenced by trends in the Si-H coupling constant and the infrared stretching frequency of the Si-H bond, as well as by X-ray crystallography and theoretical calculations. The adduct's reactivity with nucleophiles demonstrates conclusively the role of this species in metal-free 'frustrated-Lewis-pair' hydrosilylation reactions.
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