Hydrosilylation of Alkynes Mediated by N-Heterocyclic Carbene Platinum(0) Complexes

The hydrosilylation of terminal alkynes by silanes catalyzed by N-heterocyclic carbene platinum(0) complexes has been investigated. The alkynes included 1-octyne and phenylacetylene. The silanes investigated were bis(trimethylsilyloxy)methylsilane, (trimethylsilyloxy)dimethylsilane, tert-butyldimeth...

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Bibliographic Details
Published in:Organometallics 2006-04, Vol.25 (8), p.1881-1890
Main Authors: De Bo, Guillaume, Berthon-Gelloz, Guillaume, Tinant, Bernard, Markó, István E
Format: Article
Language:English
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Summary:The hydrosilylation of terminal alkynes by silanes catalyzed by N-heterocyclic carbene platinum(0) complexes has been investigated. The alkynes included 1-octyne and phenylacetylene. The silanes investigated were bis(trimethylsilyloxy)methylsilane, (trimethylsilyloxy)dimethylsilane, tert-butyldimethylsilane, triphenylsilane, phenyldimethylsilane, triethylsilane, and triethoxysilane. X-ray crystal structures for [Pt(N,N‘-dicyclohexylimidazol-2-ylidene)(η2-dimethylacetylenedicarboxylate)2] (8) and [Pt{C(E)C(E)−C(E)C(E)}(N,N‘-dimethylbenzimidazol-2-ylidene)(σ-NCCH3)] (10) (E = CO2Me) have been obtained. A selectivity model, based on structural parameters of the N-heterocyclic carbene, has been devised in order to rationalize the observed regioselectivity obtained. By a judicious choice of catalyst, alkyne, and silane, the regioselectivity of the addition can be controlled.
ISSN:0276-7333
1520-6041
DOI:10.1021/om050866j