The hydrosilation of olefins such as styrene, 1-hexene, and 2-pentene with diphenylsilane can be carried out with catalysts generated from zirconocene dichloride and two equivalents of butyllithium. Complete regioselectivity is observed as only terminal organosilicon products are produced (∼ 90%). In the case of styrene, three major products are formed: diphenylphenethylsilane (77%), trans-1-diphenylsilyl-2-phenylethene (16%), and ethylbenzene (7%). The product distribution was found to be dependent on reagent concentrations: reactions run with excess diphenylsilane favored diphenylphenethylsilane; excess styrene favored trans-1-diphenylsilyl-2-phenylethene. Extensive H/D exchange is observed in the hydrosilation of styrene with Ph2SiD2.
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Kesti et al. (1991) studied this question.
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