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Mechanistic Insights about the Ligand‐Enabled Oxy‐arylation/vinylation of Alkenes via Au(I)/Au(III) Catalysis

Abstract : The mechanism of oxy-arylation/vinylation of alkenes catalyzed by the (MeDalphos)AuCl complex was comprehensively investigated by DFT. (P,N)Au(Ph) 2 + and (P,N)Au(vinyl) 2 + are key intermediates accounting for the activation of the alkenols and for their cyclization by outersphere nucleophilic attack of oxygen. The 5-exo and 6-endo paths have been computed and compared, reproducing the peculiar regioselectivity difference observed experimentally between 4-penten-1-ol, (E) and (Z)-4-hexen-1-ols. Examining the way the alkenol coordinates to gold (more η 2 or η 1) can offer, in some cases, a simple way to predict the favored path of cyclization.
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Submitted on : Tuesday, September 20, 2022 - 10:14:19 AM
Last modification on : Wednesday, September 21, 2022 - 3:57:28 AM

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Mathilde Rigoulet, Karinne Miqueu, Didier Bourissou. Mechanistic Insights about the Ligand‐Enabled Oxy‐arylation/vinylation of Alkenes via Au(I)/Au(III) Catalysis. Chemistry - A European Journal, Wiley-VCH Verlag, 2022, pp.e202202110. ⟨10.1002/chem.202202110⟩. ⟨hal-03781154⟩

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