Palladium-Catalyzed C–H Arylation of Indoles at the C7 Position

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• 作者：Youqing Yang ; Xiaodong Qiu ; Yue Zhao ; Yucheng Mu ; Zhuangzhi Shi
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：January 20, 2016
• 年：2016
• 卷：138
• 期：2
• 页码：495-498
• 全文大小：479K
• ISSN：1520-5126

文摘

In the past decade, direct C–H arylation of indoles has been developed with high selectivity at the C2 and C3 positions via transition-metal-catalyzed cross-coupling reactions. Here we show that C–H activation can be directed to the C7 position with high selectivity in Pd-catalyzed coupling of indoles with arylboronic acids. The key to this high regioselectivity is the appropriate choice of a phosphinoyl directing group and a pyridine-type ligand in the presence of Pd(OAc)₂ catalyst. This previously elusive transformation should provide insight for the design of other cross-couplings as well.