Copper-Catalyzed Domino Rearrangement/Dehydrogenation Oxidation/Carbene Oxidation for One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans

Hua Cao, Huanfeng Jiang*, Wenjuan Yao and Xiaohang Liu

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

H. Cao, H. Jiang, W. Yao, X. Liu, Org. Lett., 2009, 11, 1931-1933.

DOI: 10.1021/ol900364y

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Abstract

A mild and efficient domino reaction allows a regiospecific synthesis of polysubstituted furans in moderate yields via a copper(I)-catalyzed rearrangement/dehydrogenation oxidation/carbene oxidation sequence of 1,5-enynes in situ formed from alkynols and diethyl but-2-ynedioate.

see article for more examples

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Synthetic Approach to Polysubstituted Furans: An Efficient Addition/Oxidative Cyclization of Alkynoates and 1,3-Dicarbonyl Compounds

W. Liu, H. Jiang, M. Zhang, C. Qi, J. Org. Chem., 2010, 75, 966-968.

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Key Words

Furans, Oxygen

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ID: J54-Y2009-1410