Issue 28, 2017
From the journal:

Organic & Biomolecular Chemistry

One-step synthesis of conjugated enynenitriles from bromocyanoacetylene†

Romain Ligny,a   Etienne S. Gauthier,a   Manuel Yáñez, ORCID logo b   Thierry Roisnel,c   Jean-Claude Guillemin ORCID logo a  and  Yann Trolez ORCID logo *a  

* Corresponding authors

a Ecole Nationale Supérieure de Chimie de Rennes, UMR 6226, CNRS, 11 allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France
E-mail: yann.trolez@ensc-rennes.fr
Tel: +33 2 23 23 80 69

b Departamento de Química, Módulo 13 and Institute of Advanced Chemical Sciences (IadChem), Universidad Autónoma de Madrid, Campus de Excelencia UAM-CSIC, Cantoblanco, 28049 Madrid, Spain

c Centre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, CNRS (UMR 6226), Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France

Abstract

The chemical reactivity of bromocyanoacetylene has been evaluated for the first time by making it react with terminal alkynes and secondary amines in the presence of bis(triphenylphosphine)palladium dichloride and copper iodide as co-catalysts. This reaction provides new conjugated enynenitriles stereoselectively in one step in variable yields.

Graphical abstract: One-step synthesis of conjugated enynenitriles from bromocyanoacetylene

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Article information

DOI
https://doi.org/10.1039/C6OB02590K
Article type
Paper
Submitted
25 Nov 2016
Accepted
27 Jun 2017
First published
06 Jul 2017

Org. Biomol. Chem., 2017,15, 6050-6056

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One-step synthesis of conjugated enynenitriles from bromocyanoacetylene

R. Ligny, E. S. Gauthier, M. Yáñez, T. Roisnel, J. Guillemin and Y. Trolez, Org. Biomol. Chem., 2017, 15, 6050 DOI: 10.1039/C6OB02590K

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