Copper-Catalyzed Three-Component Reaction for Regioselective Aryl- and Heteroarylselenation of Indoles using Selenium Powder

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• 作者：Dongping Luo ; Ge Wu ; Hang Yang ; Miaochang Liu ; Wenxia Gao ; Xiaobo Huang ; Jiuxi Chen ; Huayue Wu
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：June 3, 2016
• 年：2016
• 卷：81
• 期：11
• 页码：4485-4493
• 全文大小：471K
• 年卷期：0
• ISSN：1520-6904

文摘

A new and efficient copper-catalyzed C₃ aryl- and heteroarylselenation of indoles employing selenium powder has been developed. The advantages of this chemistry involve the use of cheap selenating reagents, tolerance of a variety of functional groups, and practicality. In addition, this protocol has been further elaborated in an intramolecular phenylselenation of a (hetero) aryl C–H bond to construct an important motif of benzoselenopheno[3,2-b]indole. A preliminary mechanism study suggests that the reaction starts with a Ullman-type selenation between aryl iodides and selenium, followed by an oxidative cross-coupling with indole. The utility of this method has been demonstrated in an efficient gram-scale synthesis and an application to the synthesis of tubulin polymerization inhibitor.