Synlett 2013; 24(20): 2715-2719
DOI: 10.1055/s-0033-1339891
letter
© Georg Thieme Verlag Stuttgart · New York

Unsymmetrical Coupling of 1-Chloroalkynes and Terminal Alkynes under ­Experimental Sonogashira Conditions

Mikkel Andreas Christensen
Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark, Fax: +4535320212   Email: mbn@kiku.dk
,
Morten Rimmen
Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark, Fax: +4535320212   Email: mbn@kiku.dk
,
Mogens Brøndsted Nielsen*
Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark, Fax: +4535320212   Email: mbn@kiku.dk
› Author Affiliations
Further Information

Publication History

Received: 23 August 2013

Accepted: 05 September 2013

Publication Date:
16 October 2013 (online)


Abstract

The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

Supporting Information

 
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