DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)
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- 作者：Zheng-Lin Wang ; Hong-Liang Li ; Li-Shi Ge ; Xing-Lan An ; Zi-Gang Zhang ; Xiaoyan Luo ; John S. Fossey ; Wei-Ping Deng
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：February 7, 2014
- 年：2014
- 卷：79
- 期：3
- 页码：1156-1165
- 全文大小：517K
- ISSN：1520-6904
文摘
A facile oxidative coupling of 伪-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available 尾-diketones, simple ketones, and 尾-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C鈥揅 bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.