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Silica Gel Promotes Reductions of Aldehydes and Ketones by N-Heterocyclic Carbene Boranes

Tsuyoshi Taniguchi and Dennis P. Curran*

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States, Email: curranpitt.edu

T. Taniguchi, D. P. Curran, Org. Lett., 2012, 14, 4540-4543.

DOI: 10.1021/ol302010f (free Supporting Information)


Abstract

NHC-boranes such as 1,3-dimethylimidazol-2-ylidine trihydridoborane serve as practical hydride donors for the reduction of aldehydes and ketones in the presence of silica gel to give alcohols in good yields under ambient conditions. Aldehydes are selectively reduced in the presence of ketones. The process is attractive because all the components are stable and easy to handle and because the isolation procedure is convenient.

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N-Heterocyclic Carbene Boranes are Good Hydride Donors

M. Horn, H. Mayr, E. Lacôte, E. Merling, J. Deaner, S. Well, T. McFadden, D. P. Curran, Org. Lett., 2012, 14, 82-85.


Key Words

1,3-Dimethylimidazol-2-ylidene borane, Reduction of Carbonyl Compounds


ID: J54-Y2012-2910