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 αand γ-substituted allyl substrates. It takes the advantage of the hemilabile character of the P ∧ N ligand. The C(sp 2 )−C(sp 3 ) 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.
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