| 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 |
| Contributors: |
Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA); Institut de Chimie de Toulouse (ICT); Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3); Communauté d'universités et établissements de Toulouse (Comue de Toulouse)-Communauté d'universités et établissements de Toulouse (Comue de Toulouse)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP); Communauté d'universités et établissements de Toulouse (Comue de Toulouse)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3); Communauté d'universités et établissements de Toulouse (Comue de Toulouse)-Centre National de la Recherche Scientifique (CNRS); Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux (IPREM); Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS); ANR-19-CE07-0037,Gold-III,Chimie de l'or(III)(2019) |
| Source: |
ISSN: 0947-6539. |
| Publisher Information: |
CCSD; Wiley-VCH Verlag |
| Publication Year: |
2022 |
| Collection: |
Université Toulouse III - Paul Sabatier: HAL-UPS |
| Subject Terms: |
·regioselectivity; ·mechanism; ·gold; ·functional theory; complexdensity; [CHIM]Chemical Sciences; [CHIM.MATE]Chemical Sciences/Material chemistry; [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry |
| Description: |
International audience ; 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. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| DOI: |
10.1002/chem.202202110 |
| Availability: |
https://univ-pau.hal.science/hal-03781154; https://univ-pau.hal.science/hal-03781154v1/document; https://univ-pau.hal.science/hal-03781154v1/file/Chemistry%20A%20European%20J%20-%202022%20-%20Rigoulet%20-%20Mechanistic%20Insights%20about%20the%20Ligand%E2%80%90Enabled%20Oxy%E2%80%90arylation%20vinylation%20of.pdf; https://doi.org/10.1002/chem.202202110 |
| Rights: |
info:eu-repo/semantics/OpenAccess |
| Accession Number: |
edsbas.344D9355 |
| Database: |
BASE |