Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides

Abdallah Zeineddine, Laura Estévez, Sonia Mallet-Ladeira, Karinne Miqueu, Abderrahmane Amgoune () and Didier Bourissou ()
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Abdallah Zeineddine: CNRS, Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069)
Laura Estévez: Institut des Sciences Analytiques et de Physico-Chimie pour l’environnement et les Matériaux (IPREM UMR 5254), Hélioparc
Sonia Mallet-Ladeira: Institut de Chimie de Toulouse (FR 2599)
Karinne Miqueu: Institut des Sciences Analytiques et de Physico-Chimie pour l’environnement et les Matériaux (IPREM UMR 5254), Hélioparc
Abderrahmane Amgoune: CNRS, Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069)
Didier Bourissou: CNRS, Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069)

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract The reluctance of gold to achieve oxidative addition reaction is considered as an intrinsic limitation for the development of gold-catalyzed cross-coupling reactions with simple and ubiquitous aryl halide electrophiles. Here, we report the rational construction of a Au(I)/Au(III) catalytic cycle involving a sequence of Csp2–X oxidative addition, Csp2–H auration and reductive elimination, allowing a gold-catalyzed direct arylation of arenes with aryl halides. Key to this discovery is the use of Me-Dalphos, a simple ancillary (P,N) ligand, that allows the bottleneck oxidative addition of aryl iodides and bromides to readily proceed under mild conditions. The hemilabile character of the amino group plays a crucial role in this transformation, as substantiated by density functional theory calculations.

Date: 2017
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DOI: 10.1038/s41467-017-00672-8

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