KOtBu-Mediated Coupling of Indoles and [60]Fullerene: Transition-Metal-Free and General Synthesis of 1,2-(3-Indole)(hydro)[60]fullerenes

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• 作者：Fei Li ; Imad Elddin Haj Elhussin ; Shengli Li ; Hongping Zhou ; Jieying Wu ; Yupeng Tian
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：80
• 期：21
• 页码：10605-10610
• 全文大小：326K
• ISSN：1520-6904

文摘

Direct coupling of indoles with C₆₀ has been achieved for the first time. Transition-metal-free KO^tBu-mediated reaction of indoles to [60]fullerene has been developed as a practical and efficient method for the synthesis of various 1,2-(3-indole)(hydro)[60]fullerenes that are otherwise difficult to direct synthesize in an efficient and selective manner. This methodology tolerates sensitive functionalities such as chloro, ester, and nitro on indole and builds molecular complexity rapidly, with most reactions reaching completion in <1 h. A plausible reaction mechanism is proposed to explain the high regioselectivity at the 3-position of the indoles and the formation of 1,2-(3-indole)(hydro)[60]fullerenes.