Oxidative addition of carbon-carbon bonds to gold

Maximilian Joost; Laura Estévez; Karinne Miqueu; Abderrahmane Amgoune; Didier Bourissou

doi:10.1002/anie.201500458

Oxidative addition of carbon-carbon bonds to gold

Angew Chem Int Ed Engl. 2015 Apr 20;54(17):5236-40. doi: 10.1002/anie.201500458. Epub 2015 Feb 26.

Authors

Maximilian Joost¹, Laura Estévez, Karinne Miqueu, Abderrahmane Amgoune, Didier Bourissou

Affiliation

¹ Laboratoire Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier/CNRS UMR 5069, 118 Route de Narbonne, 31062 Toulouse Cedex 09 (France).

PMID: 25727203
DOI: 10.1002/anie.201500458

Abstract

The oxidative addition of strained CC bonds (biphenylene, benzocyclobutenone) to DPCb (diphosphino-carborane) 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.

Keywords: CC bond activation; gold chemistry; oxidative addition; reductive elimination; selectivity.