A New Route to <i>E</i> ‐Stilbenes through the Transition‐Metal‐Free KO <i>t</i> Bu/DMF‐Promoted Direct Coupling of Alcohols with Phenyl Acetonitriles - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

A New Route to E ‐Stilbenes through the Transition‐Metal‐Free KO t Bu/DMF‐Promoted Direct Coupling of Alcohols with Phenyl Acetonitriles

Résumé

An alternative route to synthesise alkenes, based only on the KO t Bu/DMF promoted activation and direct coupling of alcohols with phenyl acetonitriles, is reported. Various E-stilbenes have thus been obtained directly from alcohols that are sustainable sources of carbon, which to our knowledge, is unprecedented in the absence of transition metal based catalysts. A variation allowing, through a Csp 3 À Csp 3 bond formation, the selective synthesis of N-Heteroarenes is also described. A mechanism for the olefination pathway proceeding via an original activation of alcohols under alkyl formates is provided.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
Eur J Org Chem - 2022 - Liu - A New Route to E‐Stilbenes through the Transition‐Metal‐Free KOtBu DMF‐Promoted Direct.pdf (5.48 Mo) Télécharger le fichier
Origine : Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

hal-03871591 , version 1 (25-11-2022)

Identifiants

Citer

Xiaoping Liu, Jean-Marc Sotiropoulos, Marc Taillefer. A New Route to E ‐Stilbenes through the Transition‐Metal‐Free KO t Bu/DMF‐Promoted Direct Coupling of Alcohols with Phenyl Acetonitriles. European Journal of Organic Chemistry, 2022, 2022 (26), pp.e202200631. ⟨10.1002/ejoc.202200631⟩. ⟨hal-03871591⟩
20 Consultations
11 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More