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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)(η 2 -dimethylacetylenedicarboxylate) 2 ] ( 8 ) and [Pt{C(E) C(E)−C(E) C(E)}( N, N ‘-dimethylbenzimidazol-2-ylidene)(σ-NCCH 3 )] ( 10 ) (E = CO 2 Me) 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.
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Bo et al. (2006) studied this question.
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