Premium
Linking Borane with N‐Heterocyclic Carbenes: Effective Hydrogen‐Atom Donors for Radical Reactions
Author(s) -
Walton John C.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805362
Subject(s) - borane , chemistry , deoxygenation , azobisisobutyronitrile , medicinal chemistry , hydrogen bond , combinatorial chemistry , photochemistry , polymer chemistry , catalysis , organic chemistry , molecule , polymer , polymerization
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–BH 3 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.