Copper-Catalysed Hydroamination of N-Allenylsulfonamides: The Key Role of Ancillary Coordinating Groups - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2019

Copper-Catalysed Hydroamination of N-Allenylsulfonamides: The Key Role of Ancillary Coordinating Groups

Résumé

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.
Fichier principal
Vignette du fichier
s-0037-1611673.pdf (1.15 Mo) Télécharger le fichier
Origine : Fichiers éditeurs autorisés sur une archive ouverte
Loading...

Dates et versions

hal-02075687 , version 1 (21-03-2019)

Licence

Paternité - Pas d'utilisation commerciale - Pas de modification

Identifiants

Citer

Rémi Blieck, Luca Perego, Ilaria Ciofini, Laurence Grimaud, Marc Taillefer, et al.. Copper-Catalysed Hydroamination of N-Allenylsulfonamides: The Key Role of Ancillary Coordinating Groups. Synthesis: Journal of Synthetic Organic Chemistry, 2019, 51 (05), pp.1225-1234. ⟨10.1055/s-0037-1611673⟩. ⟨hal-02075687⟩
69 Consultations
102 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More