Synthesis 2012; 44(10): 1491-1500
DOI: 10.1055/s-0031-1289760
special topic
© Georg Thieme Verlag Stuttgart · New York

Oxidative Alkynylation of Imines with Alkynylcopper Reagents: A Straightforward and Practical Entry to Ynimines

Anouar Laouiti
a  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
b  Laboratoire de Chimie Organique Hétérocyclique, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’environnement, 5019 Monastir, Tunisia
,
Kévin Jouvin
a  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
,
Flavien Bourdreux
a  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
,
Mohamed M. Rammah
b  Laboratoire de Chimie Organique Hétérocyclique, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’environnement, 5019 Monastir, Tunisia
,
Mohamed B. Rammah
b  Laboratoire de Chimie Organique Hétérocyclique, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’environnement, 5019 Monastir, Tunisia
,
Gwilherm Evano*
a  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
c  Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles, Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium, Fax: +32(2)6502798   Email: gevano@ulb.ac.be
› Author Affiliations
Further Information

Publication History

Received: 29 February 2012

Accepted after revision: 07 March 2012

Publication Date:
12 April 2012 (online)

Abstract

We have developed an efficient and general synthesis of ynimines based on an oxidative cross-coupling between imines and alkynylcopper reagents. Upon simple addition of 1,2-dimethylimidazole in the presence of oxygen, these bench-stable, crystalline, and readily available polymeric compounds were found to be especially suitable reagents for the introduction of an alkynyl group into a wide range of ketimines at room temperature and under especially mild conditions.

Supporting Information

 
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