Au(I)/Au(III) Catalytic Allylation Involving π-Allyl Au(III) Complexes

Jessica Rodriguez; David Vesseur; Alexis Tabey; Sonia Mallet-Ladeira; Karinne Miqueu; Didier Bourissou

doi:10.1021/acscatal.1c04580

Journal articles

Au(I)/Au(III) Catalytic Allylation Involving π-Allyl Au(III) Complexes

Jessica Rodriguez David Vesseur Alexis Tabey Sonia Mallet-Ladeira Karinne Miqueu ¹ Didier Bourissou ^{2, *}

* Corresponding author

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

2 LHFA - Laboratoire Hétérochimie Fondamentale et Appliquée

Abstract : A (MeDalphos)AuCl complex was found to efficiently catalyze the cross-coupling of indoles and allyl acetates/alcohols. The reaction tolerates many functional groups and selectively affords the branched C3-allylated products from both α- and γ-substituted allyl substrates. It takes the advantage of the hemilabile character of the P∧N ligand. The C(sp2)-C(sp3) coupling operates via a Au(I)/Au(III) redox cycle and involves a dicationic π-allyl Au(III) complex as a key intermediate. In this case, the allyl moiety adopts an asymmetric σ + π-coordination mode, as substantiated by NMR spectroscopy and density functional theory (DFT) calculations.

Keywords : (P∧N) ligands gold homogeneous catalysis indoles π-allyl

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Journal articles

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Chemical Sciences

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Submitted on : Tuesday, January 25, 2022 - 9:41:54 PM
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Au(I)/Au(III) Catalytic Allylation Involving π-Allyl Au(III) Complexes

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Au(I)/Au(III) Catalytic Allylation Involving π-Allyl Au(III) Complexes

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