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Synthesis 2011(17): 2789-2795  
DOI: 10.1055/s-0030-1260126
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Iodoethynes with Arylboronic Acids under Aerobic Conditions

Jian-Sheng Tang*a,b, Ye-Xiang Xieb, Zhi-Qiang Wangc, Jin-Heng Li*b
a Mathematics and Science Department, Hunan First Normal University, Changsha 410205, P. R. of China
b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China
Fax: +86(731)88872531; e-Mail: jhli@hunnu.edu.cn; e-Mail: hnyztjs@163.com;
c Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
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Publication History

Received 28 April 2011
Publication Date:
18 July 2011 (online)

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Abstract

Ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling of iodoethynes with arylboronic acids under aerobic conditions has been developed. In the presence of palladium(II) acetate and cesium carbonate, a variety of iodoethynes underwent the Suzuki­-Miyaura cross-coupling reaction with arylboronic acids at room temperature to afford the corresponding internal alkynes in moderate to good yields. It is noteworthy that this protocol proceeds under mild and aerobic conditions without the aid of ligands.

Key words

palladium - iodoethynes - arylboronic acids - Suzuki-Miyaura - cross-coupling - alkynes