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

Author

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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
    Facultade de Química Lagoas-Marcosende s/n)

  • 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))

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.

Suggested Citation

  • Abdallah Zeineddine & Laura Estévez & Sonia Mallet-Ladeira & Karinne Miqueu & Abderrahmane Amgoune & Didier Bourissou, 2017. "Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides," Nature Communications, Nature, vol. 8(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_s41467-017-00672-8
    DOI: 10.1038/s41467-017-00672-8
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    Cited by:

    1. Shuyao Zhang & Jingwen Wei & Xiaohan Ye & Angel Perez & Xiaodong Shi, 2023. "Accessing gold p-acid reactivity under electrochemical anode oxidation (EAO) through oxidation relay," Nature Communications, Nature, vol. 14(1), pages 1-8, December.

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