Abstract
A full account of our studies on internal alkyne hydrosilylations using platinum catalysis is described. We demonstrate that these transformations are highly governed by the electronic characteristics of the alkyne substituents, wherein the hydride will add preferentially to the more electron-deficient alkyne carbon. The steric and coordinative capabilities of the substituents influence the selectivity to a much lesser extent, with propargylic alcohols a lone exception. The choice of silane is relevant in some cases; specific silanes will afford high regioselectivities while others are much less selective. Ultimately, the regioselectivity of addition can be quite predictable using 13C NMR chemical shift data, allowing this reactivity to be incorporated into purposeful reaction design.
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