Alkyl boronate esters are useful intermediates in synthetic chemistry because of the many transformations that can convert carbon-boron bonds to carbon-carbon or carbon-heteroatom bonds. These compounds are typically synthesized by the hydroboration of alkenes, but the regioselective synthesis of secondary alkyl boronates by this method is often challenging. We report the borylation of the primary and secondary alkyl C-H bonds of hydrosilanes catalyzed by an Ir complex that occurs to form alkyl boronate esters with high selectivity for the borylation of C-H bonds γ to the hydrosilyl group. The borylation of the secondary C-H bonds of hydrosilanes derived from 1,1-disubstituted alkenes forms the corresponding secondary alkyl boronate esters with high diastereoselectivity. The synthetic utility of the hydrosilyl-containing alkyl boronates esters formed by this method is demonstrated by site selective transformations at the carbon-boron and carbon-silicon bonds of these products.

Iridium-catalyzed borylation of unactivated alkyl C-H bonds directed by a hydrosilyl group

251st National Meeting (2016)

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