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- Title
Mechanistic Insights about the Ligand‐Enabled Oxy‐arylation/vinylation of Alkenes via Au(I)/Au(III) Catalysis.
- Authors
Rigoulet, Mathilde; Miqueu, Karinne; Bourissou, Didier
- 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 outer‐sphere 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 η2 or η1) can offer, in some cases, a simple way to predict the favored path of cyclization.
- Subjects
ALKENES; CATALYSIS; ARYLATION; ENOLS; RING formation (Chemistry)
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 60, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202202110