Silica gel promotes reductions of aldehydes and ketones by N-heterocyclic carbene boranes.

Tsuyoshi Taniguchi, Dennis P Curran

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Organic letters 2012 Sep 7

filter terms:

N-Heterocyclic carbene boranes (NHC-boranes) such as 1,3-dimethylimidazol-2-ylidine trihydridoborane (diMe-Imd-BH(3)) serve as practical hydride donors for the reduction of aldehydes and ketones in the presence of silica gel. Primary and secondary alcohols are formed in good yields under ambient conditions. Aldehydes are selectively reduced in the presence of ketones. One, two, or even all three of the boron hydrides can be transferred. The process is attractive because all the components are stable and easy to handle and because both the reaction and isolation procedures are convenient.

Citation

Tsuyoshi Taniguchi, Dennis P Curran. Silica gel promotes reductions of aldehydes and ketones by N-heterocyclic carbene boranes. Organic letters. 2012 Sep 7;14(17):4540-3