| Title: |
Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π‐Alkene Activation |
| Authors: |
Rigoulet, Mathilde; Thillaye Du Boullay, Olivier; Amgoune, Abderrahmane; 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); ANR-16-CE07-0027,CHAUCACAO,Activation electrophile et fonctionnalisation de liaisons C-H avec des complexes d'or de haut degré d'oxydation(2016) |
| Source: |
ISSN: 1433-7851. |
| Publisher Information: |
CCSD; Wiley-VCH Verlag |
| Publication Year: |
2020 |
| Collection: |
Université Toulouse III - Paul Sabatier: HAL-UPS |
| Subject Terms: |
N) Ligand; (P; π-Activation; Oxidative addition; Homogeneous catalysis; Gold; [CHIM]Chemical Sciences |
| Description: |
International audience ; The hetero-arylation of alkenes with aryl iodides has been efficiently achieved with the (MeDalphos)AuCl complex via Au(I)/Au(III) catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5, 6 and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox / oxidative approaches. In addition, it actuates a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| DOI: |
10.1002/anie.202006074 |
| Availability: |
https://hal.science/hal-03005073; https://hal.science/hal-03005073v1/document; https://hal.science/hal-03005073v1/file/HAL%20Heteroarylation%20Au.pdf; https://doi.org/10.1002/anie.202006074 |
| Rights: |
info:eu-repo/semantics/OpenAccess |
| Accession Number: |
edsbas.4D06183 |
| Database: |
BASE |