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Synthesis 2012(4): 541-546  
DOI: 10.1055/s-0031-1290159
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Palladium-Catalyzed Cross-Coupling Reaction of Alkynyl Halides with Organoboronic Acids under Aerobic Conditions

Jian-Sheng Tang*a,b, Mi Tiana, Wen-Bing Shenga, Can-Cheng Guo*a
a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China
Fax: +86(731)88821488; e-Mail: ccguo@hnu.edu.cn;
b Mathematics and Science Department, Hunan First Normal University, Changsha 410205, P. R. of China
Fax: +86(731)82841056; e-Mail: hnyztjs@163.com;
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Publication History

Received 12 November 2011
Publication Date:
16 January 2012 (online)

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Abstract

Ligand-free palladium-catalyzed cross-coupling reaction of alkynyl halides with organoboronic acids under aerobic conditions has been developed. In the presence of bis(dibenzylideneacetone)palladium(0) and cesium carbonate, a variety of alkynyl halides (I, Br, and Cl) underwent the Suzuki-Miyaura cross-­coupling reaction with organoboronic acids at room temperature to afford the corresponding unsymmetrical diarylalkynes in moderate to good yields. It is noteworthy that this is first report on the reaction of alkynyl chlorides with arylboronic acids.

Key words

palladium - alkynyl halides - organoboronic acids - cross-coupling reaction - alkynes

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