Green Chemistry [LASYROC]

Abstract:

A copper-catalysed three-component coupling reaction between a carbonyl derivative, a terminal ynamide and an amine has been developed for the one-pot green construction of γ-amino-ynamides from simple starting materials and with a broad functional group tolerance.The copper-zeolite-catalysed three-component coupling reaction between an aldehyde or a ketone, a terminal ynamide and an amine is reported. The so-elaborated methods, dubbed AYA (i.e. Aldehyde-Ynamide-Amine) and KYA (i.e. Ketone-Ynamide-Amine), enable the straightforward one-pot synthesis of γ-amino-ynamides from simple starting materials and with a broad functional group tolerance. Moreover, AYA/KYA processes are performed at room temperature under solvent-free conditions or in ethyl acetate as green solvent in the presence of a copper-based easy-to-recover/-remove catalyst, at low loading (3 mol%), making these synthetic methods fully green.

 

Reference :

Fabian Schlimpen, Tun Ast, Valérie Bénéteau, Patrick Pale and Stefan Chassaing

From A³/KA² to AYA/KYA multicomponent coupling reactions with terminal ynamides as alkyne surrogates – a direct, green route to γ-amino-ynamides

Green Chem., 2022,24, 6467-6475- DOI: https://doi.org/10.1039/D2GC00966H

 

Contacts:

Fabian Schlimpen, Patrick Pale & Stefan Chassaing,, LASYROC, Institut de Chimie de Strasbourg (UMR 7177).