Linking Borane with N-Heterocyclic Carbenes: Effective Hydrogen-Atom Donors for Radical Reactions

Linking Borane with N-Heterocyclic Carbenes: Effective Hydrogen-Atom Donors for Radical Reactions

Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the B---H 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 r...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-02, Vol.48 (10), p.1726-1728
1. Verfasser: Walton, John C
Format: Artikel
Sprache:eng
Schlagworte:
boron
CH activation
N-heterocyclic carbenes
radicals
reduction
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Zusammenfassung:Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the B---H 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200805362