From Benzofurans to Indoles: Palladium-Catalyzed Reductive Ring-Opening and Closure via β-Phenoxide Elimination - Processus d'activation sélective par transfert d'énergie uni-électronique ou radiatif Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2018

From Benzofurans to Indoles: Palladium-Catalyzed Reductive Ring-Opening and Closure via β-Phenoxide Elimination

Résumé

Benzofurans can undergo ring-opening by a palladium-catalyzed process resulting in C−O bond breaking. Benzofuran-tethered 2-iodoanilines give synthetically interesting 2-(3-indolylmethyl)phenols in an overall reductive process. Mechanistic studies suggest that this unusual reaction proceeds by carbopalladation of benzofuran giving a 3-palladated 2,3-dihydrobenzofuran intermediate, which then fragments by an uncommon trans-elimination of the phenoxide group β to the metal. In this transformation, N,N-diisopropylethylamine (DIPEA) acts as a base and as a reducing agent: it regenerates palladium(0) from palladium(II), thus allowing catalytic turnover.
Fichier principal
Vignette du fichier
Draft_REVISED_final.pdf (872.88 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-01913160 , version 1 (07-01-2022)

Identifiants

Citer

Luca Alessandro Perego, Simon Wagschal, Raymond Grüber, Paul Fleurat-Lessard, Laurent El Kaim, et al.. From Benzofurans to Indoles: Palladium-Catalyzed Reductive Ring-Opening and Closure via β-Phenoxide Elimination. Advanced Synthesis and Catalysis, 2018, 361 (1), pp.151-159. ⟨10.1002/adsc.201801225⟩. ⟨hal-01913160⟩
129 Consultations
94 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More