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
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
复制标题
通过C-H活化的吲哚与丙烯酸酯的机械化学活化氧化偶联：3-乙烯基吲哚和β,β-二吲哚基丙酸酯的合成及其机理研究
DOI：
10.1021/acs.joc.6b01138
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发表时间：
2016-07-15
影响因子：
3.6
通讯作者：
Su, Wei-Ke
中科院分区：
文献类型：
--
作者：
Jia, Kan-Yan;Yu, Jing-Bo;Su, Wei-Ke
在高速球磨条件下，通过无溶剂C-H官能化，探索了3-乙烯基吲哚（3）和β，β-二吲哚基丙酸酯（4）的构建。反应选择性受催化剂的显著影响：Pd（OAc）（2）以中等至良好的产率提供3，而PdX 2（X = Cl，I）提供4作为主要产物。反应机理已被进一步研究，通过使用电喷雾电离质谱，暗示的二聚体钯配合物A作为关键中间体的选择性的解释。
Construction of 3-vinylindoles (3) and beta,beta-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.