Currently, reduction reactions are hindered by a lack of functional group tolerance when using traditional reducing agents like lithium and aluminum hydrides and catalytic hydrogenations.  As a result, reactions such as the Luche reduction, and more recently hydrosilations, have been developed. However, these cannot selectively reduce aldehydes in the presence of similar carbonyl functional groups. Herein, we report a reaction that selectively reduces aldehydes or ketones in the presence of other readily reduced functional groups.  Using a copper catalyst and disilane as a terminal reductant, aldehydes and ketones were reduced to alcohols via a mechanism involving a 1,2-Brook Rearrangement. This method can selectively reduce aldehydes over ketones when both functional groups are present and allows for a broad substrate scope.

Copper-catalyzed selective reduction of aldehydes and ketones using a disilane as a terminal reductant

ACS Spring Meeting 2021

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