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Gold‐Catalyzed Allylation of Aryl Boronic Acids: Accessing Cross‐Coupling Reactivity with Gold
Author(s) -
Levin Mark D.,
Toste F. Dean
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402924
Subject(s) - transmetalation , bimetallic strip , catalysis , reductive elimination , chemistry , aryl , ligand (biochemistry) , combinatorial chemistry , reactivity (psychology) , coupling reaction , oxidative addition , amine gas treating , organic chemistry , medicine , biochemistry , alkyl , receptor , alternative medicine , pathology
A sp 3 –sp 2 CC cross‐coupling reaction catalyzed by gold in the absence of a sacrificial oxidant is described. Vital to the success of this method is the implementation of a bimetallic catalyst bearing a bis(phosphino)amine ligand. A mechanistic hypothesis is presented, and observable transmetalation, CBr oxidative addition, and CC reductive elimination in a model gold complex are shown. We expect that this method will serve as a platform for the development of novel transformations involving redox‐active gold catalysts.