4.8 Article

Oxidative Addition of Carbon-Carbon Bonds to Gold

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 17, Pages 5236-5240

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201500458

Keywords

C-C bond activation; gold chemistry; oxidative addition; reductive elimination; selectivity

Funding

  1. Centre National de la Recherche Scientifique
  2. Universite de Toulouse
  3. Agence Nationale de la Recherche [ANR-10-BLAN-070901]

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The oxidative addition of strained C-C bonds (biphenylene, benzocyclobutenone) to DPCb (diphosphinocarborane) gold(I) complexes is reported. The resulting cationic organogold(III) complexes have been isolated and fully characterized. Experimental conditions can be adjusted to obtain selectively acyl gold(III) complexes resulting from oxidative addition of either the C(aryl)-C(O) or C(alkyl)-C(O) bond of benzocyclobutenone. DFT calculations provide mechanistic insight into this unprecedented transformation.

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