Opening the Way to Catalytic Aminopalladation/Proxicyclic Dehydropalladation: Access to Methylidene γ-Lactams - Université Pierre et Marie Curie Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2016

Opening the Way to Catalytic Aminopalladation/Proxicyclic Dehydropalladation: Access to Methylidene γ-Lactams

Filipe J. S. Duarte
  • Fonction : Auteur
Maria José Calhorda
  • Fonction : Auteur
Julie Oble
Giovanni Poli

Résumé

A new aerobic intramolecular palladium(II)-based catalytic system that triggers aminopalladation/dehydropalladation of N-sulfonylalkenylamides to give the corresponding methylidene γ-lactams has been identified. Use of triphenylphosphine and chloride anion as ligands is mandatory for optimal yields, and molecular oxygen can be used as the sole terminal oxidant. Scope and limitations of the methods are described. A mechanism is proposed on the basis of experimental results as well as density functional theory calculations.

Domaines

Chimie
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Dates et versions

hal-01480751 , version 1 (01-03-2017)

Identifiants

Citer

Mélanie M. Lorion, Filipe J. S. Duarte, Maria José Calhorda, Julie Oble, Giovanni Poli. Opening the Way to Catalytic Aminopalladation/Proxicyclic Dehydropalladation: Access to Methylidene γ-Lactams. Organic Letters, 2016, 18 (5), pp.1020-1023. ⟨10.1021/acs.orglett.6b00143⟩. ⟨hal-01480751⟩
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