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DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)

Zheng-Lin Wang, Hong-Liang Li, Li-Shi Ge, Xing-Lan An, Zi-Gang Zhang, Xiaoyan Luo*, John S. Fossey and Wei-Ping Deng*

*Shanghai Key Laboratory of New Drug Design & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China, Email: xyluoecust.edu.cn, weiping_dengecust.edu.cn

Z.-L. Wang, H.-L. Li, L.-S. Ge, X.-L. An, Z.-G. Zhang, X. Luo, J. S. Fossey, W.-P. Deng, J. Org. Chem., 2014, 79, 1156-1165.

DOI: 10.1021/jo4026034 (free Supporting Information)


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Abstract

A facile oxidative coupling of α-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) enables the synthesis of 2,3-dicyanofurans and thiophenes from readily available β-diketones, simple ketones, and β-keto thioamides in very good yield. Mechanistic investigations revealed that a radical process and a water-promoted C-C bond cleavage could be involved in this transformation.

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Key Words

Furans, DDQ


ID: J42-Y2014