I thank EaStChem for financial support.
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Linking Borane with N-Heterocyclic Carbenes: Effective Hydrogen-Atom Donors for Radical Reactions†
Article first published online: 27 JAN 2009
DOI: 10.1002/anie.200805362
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 10, pages 1726–1728, February 23, 2009
Additional Information
How to Cite
Walton, John C. (2009), Linking Borane with N-Heterocyclic Carbenes: Effective Hydrogen-Atom Donors for Radical Reactions. Angew. Chem. Int. Ed., 48: 1726–1728. doi: 10.1002/anie.200805362
- †
Publication History
- Issue published online: 17 FEB 2009
- Article first published online: 27 JAN 2009
Funded by
- EaStChem
- Abstract
- Article
- References
- Cited By
Keywords:
- boron;
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
H activation; - N-heterocyclic carbenes;
- radicals;
- reduction
Abstract
Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the BH bonds of borane by a surprisingly large amount upon the formation of NHC–BH3 complexes. This property was exploited in the development of a suite of NHC–borane complexes for the reduction of xanthates in radical-mediated Barton–McCombie-type deoxygenation reactions (see scheme). AIBN=azobisisobutyronitrile, Bn=benzyl.