Copper-Mediated Intramolecular Oxidative C鈥揌/C鈥揌 Cross-Coupling of 伪-Oxo Ketene N,S-Acetals for Indole Synthesis

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• 作者：Fei Huang ; Ping Wu ; Liandi Wang ; Jiping Chen ; Chenglin Sun ; Zhengkun Yu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：November 7, 2014
• 年：2014
• 卷：79
• 期：21
• 页码：10553-10560
• 全文大小：436K
• ISSN：1520-6904

文摘

CuCl₂-mediated intramolecular C鈥揌/C鈥揌 cross-dehydrogenative coupling (CDC) of thioalkyl-substituted 伪-acetyl or 伪-aroyl ketene N,S-acetals afforded 2-thioalkyl indoles. Tunable C鈥揝 bond transformations of the resultant indoles led to highly functionalized N-heterocyclic compounds. A 尾-thioalkyl is necessary to activate the N,S-acetal substrate and enable the CDC reaction to occur, and the relevant mechanism studies revealed that the CDC reaction follows a radical pathway.