Linking Borane with N‐Heterocyclic Carbenes: Effective Hydrogen‐Atom Donors for Radical Reactions | Zendy

Walton John C. | Zendy

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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

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.

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