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Au(i)/Au(iii)-Catalyzed C–N coupling

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Abstract

Cycling between Au(I) and Au(III) is challenging, so gold-catalyzed cross-couplings are rare. The (MeDalphos)AuCl complex, which we showed was prone to undergo oxidative addition, is reported here to efficiently catalyze the C–N coupling of aryl iodides and amines. The transformation does not require an external oxidant or a directing group. It is robust and works with a wide scope of aryl iodides and N-nucleophiles under mild conditions. Mechanistic studies, including the NMR and MS characterization of a key aryl amido Au(III) complex, strongly support a 2e redox cycle in which oxidative addition precedes transmetalation and reductive elimination is the rate-determining step.

Graphical abstract: Au(i)/Au(iii)-Catalyzed C–N coupling

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Publication details

The article was received on 30 Sep 2019, accepted on 18 Nov 2019 and first published on 21 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC07666B
Chem. Commun., 2020, Advance Article

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    Au(I)/Au(III)-Catalyzed C–N coupling

    J. Rodriguez, N. Adet, N. Saffon-Merceron and D. Bourissou, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC07666B

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