Reduction reactions are becoming increasingly important as future carbon sources will likely be highly oxidized.  However, reduction reactions are hindered by a lack of functional group tolerance when using traditional reducing agents like boron and aluminum hydrides and hydrogen.  Unfortunately, the vast majority of reductions rely on these reducing agents.  Hypothetically, catalytic hydrogenations could be rendered selective, but few catalysts have been developed that achieve good selectivity.  Reactions such as the Luche reduction achieve selectivity by using an additive which can activate one carbonyl to be more reducible than another functional group.  More recently, hydrosilylations have been developed which adds silanes to a relatively short list of terminal reductants, however, these cannot selectively reduce aldehydes in the presence of similar carbonyl functional groups. Herein, we report a copper-catalyzed reaction that selectively reduces aldehydes or ketones in the presence of other readily reducible functional groups.  We use a disilane as a terminal reductant, which is a new class of terminal reductant.  The mechanism was studied both computationally and experimentally. The substrate scope, selectivity and mechanism will be discussed.

Selective reduction of aldehydes and ketones with a copper catalyst using a disilane as the reductant

ACS Spring 2022

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