Issue 7, 2011
From the journal:

Chemical Communications

Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides†

Xiaoyi Chen,a   Wei Kong,a   Haiting Cai,a   Lichun Konga  and  Gangguo Zhu*a  

* Corresponding authors

a Department of Chemistry, Zhejiang Normal University, 688 Yingbing Road, Jinhua 321004, PR China
E-mail: gangguo@zjnu.cn
Fax: +86 579-82282610
Tel: +86 579-82283702

Abstract

A highly efficient and selective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes viaPd-catalyzed coupling of haloalkynes and allylic halides is described. The (1E)-1,2-dihalo-1,4-dienes were generated in good yields with excellent stereoselectivities (1E/1Z up to >98/2), while (1Z)-1,2-dihalo-1,4-dienes were produced in excellent yields and stereoselectivities (1Z/1E up to >98/2) by simply adding stoichiometric lithium halides.

Graphical abstract: Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides

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Article information

DOI
https://doi.org/10.1039/C0CC04879H
Article type
Communication
Submitted
09 Nov 2010
Accepted
10 Dec 2010
First published
07 Jan 2011

Chem. Commun., 2011,47, 2164-2166

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Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides

X. Chen, W. Kong, H. Cai, L. Kong and G. Zhu, Chem. Commun., 2011, 47, 2164 DOI: 10.1039/C0CC04879H

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