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N-Heterocyclic Carbene Boranes are Good Hydride Donors

Markus Horn, Herbert Mayr*, Emmanuel Lacôte, Everett Merling, Jordan Deaner, Sarah Well, Timothy McFadden and Dennis P. Curran*

Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, D-81377 München, Germany, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States, Email: herbert.mayrcup.uni-muenchen.de, curranpitt.edu

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

DOI: 10.1021/ol202836p (free Supporting Information)



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Abstract

N-heterocyclic carbene boranes (NHC-boranes) are among the most nucleophilic classes of neutral hydride donors. Reductions of highly electron-poor C=N and C=C bonds provide hydrogenation products along with new, stable borylated products. The results suggest that NHC-boranes have considerable untapped potential as neutral organic reductants.

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

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


Key Words

1,3-Dimethylimidazol-2-ylidene borane, Reductive Amination


ID: J54-Y2012-3170