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Diethylene Glycol Serving as Ethyne Equivalent: A Sustainable Approach toward 2,3-Disubstituted Furan

Jin-Tao Yu, Bo Shi, Haibo Peng, Song Sun, Haoke Chu, Yan Jiang and Jiang Cheng*

*School of Petrochemical Engineering, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. China, Email: jiangchengcczu.edu.cn

J.-T. Yu, B. Shi, H. Peng, S. Sun, H. Chu, Y. Jiang, J. Cheng, Org. Lett., 2015, 17, 3643-3645.

DOI: 10.1021/acs.orglett.5b01521 (free Supporting Information)


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Abstract

A copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol gives 2,3-disubstituted furans in the presence of tert-butyl peroxide (TBHP) via a sequential O- and C- functionalization of β-ketoester by diethylene glycol. Diethylene glycol serves as a environmentally friendly and cheap substitute of ethyne, that releases H2O and alcohol as clean wastes.

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Key Words

Furans, tert-butyl peroxide, Green Chemistry


ID: J54-Y2015