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.mayr
cup.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
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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
