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

Oxidative addition of carbon-carbon bonds to gold

Maximilian Joost  1 , Laura Estévez, Karinne Miqueu, Abderrahmane Amgoune, Didier Bourissou
Affiliations

Oxidative addition of carbon-carbon bonds to gold

Maximilian Joost et al. Angew Chem Int Ed Engl. .

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.

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