Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C–H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism

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• 作者：Kan-Yan Jia ; Jing-Bo Yu ; Zhi-Jiang Jiang ; Wei-Ke Su
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：81
• 期：14
• 页码：6049-6055
• 全文大小：537K
• 年卷期：0
• ISSN：1520-6904

文摘

Construction of 3-vinylindoles (3) and β,β-diindolyl propionates (4) through solvent-free C–H functionalization has been explored under high-speed ball-milling conditions. The reaction selectivity is influenced by the catalyst dramatically: Pd(OAc)₂ provides 3 in moderate to good yields, whereas PdX₂ (X = Cl, I) affords 4 as the major products. The reaction mechanism has been further studied by using electrospray ionization mass spectrometry, implicating the dimeric palladium complex A as the key intermediate in an explanation of the selectivity.