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Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes

Zhengwang Chen, Gao Huang, Huanfeng Jiang*, Huawen Huang and Xiaoyan Pan

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China, Email: jianghfscut.edu.cn

Z. Chen. G. Huang, H. Jiang, H. Huang, X. Pan, J. Org. Chem., 2011, 76, 1134-1139.

DOI: 10.1021/jo1023987 (free Supporting Information)


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Abstract

2,5-Disubstituted 3-iodofurans are readily prepared under very mild reaction conditions by a palladium/copper-catalyzed cross-coupling of (Z)-β-bromoenol acetates and terminal alkynes leading to conjugated enyne acetates as intermediates in high yields, followed by iodocyclization in good yields. The resulting iodine-containing furans can be readily elaborated to 2,3,5-trisubstituted furans.

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proposed mechanism



A Highly Efficient Synthesis of 2,5-Disubstituted Furans from Enyne Acetates Catalyzed by Lewis Acid and Palladium

Z.-W. Chen, M.-T. Luo, Y.-L. Wen, M. Ye, Z.-G. Zhou, L.-X. Liu, Synlett, 2014, 25, 2341-2344.


Key Words

Furans


ID: J42-Y2011-0290