Silyl Anion Initiated Hydroboration of Aldehydes and Ketones

Abstract

Hydroboration is an emerging method for mild and selective reduction of carbonyl compounds. Typically, transition-metal or reactive main-group hydride catalysts are used in conjunction with a mild reductant such as pinacolborane. The reactivity of the main-group catalysts is a consequence of the nucleophilicity of their hydride ligands. Silicon hydrides are significantly less reactive and are therefore not efficient hydroboration catalysts. Here, a readily prepared silyl anion is reported to be an effective initiator for the reduction of aldehydes and ketones requiring mild conditions, low catalyst loadings and with a good substrate scope. The silyl anion it is shown to activate HBpin to generate a reactive borohydride in situ which reacts with aldehydes and ketones to afford the hydroboration product.