Three-Step Synthesis of 2,5,7-Trisubstituted Indoles from N-Acetyl-2,4,6-trichloroaniline Using Pd-Catalyzed Site-Selective Cross-Coupling
Three-Step Synthesis of 2,5,7-Trisubstituted Indoles from N-Acetyl-2,4,6-trichloroaniline Using Pd-Catalyzed Site-Selective Cross-Coupling
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Pd 催化位点选择性交叉偶联三步合成 N-乙酰基-2,4,6-三氯苯胺 2,5,7-三取代吲哚
DOI：
10.1039/c7ob01547j
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发表时间：
2017
影响因子：
3.2
通讯作者：
Kei Manabe
中科院分区：
文献类型：
--
作者：
3.Miyuki Yamaguchi;Kei Manabe
我们报道了从 N-乙酰基-2,4,6-三氯苯胺三步合成 2,5,7-三取代吲哚的方法，第一步采用 Pd/二羟基三联苯膦 (DHTP) 催化的邻位选择性 Sonogashira 偶联，然后环化得到 2-取代吲哚 5,7-二氯吲哚。随后通过 Pd/DHTP 催化的位点选择性 Kumada-Tamao-Corriu 偶联在 C7 位引入芳基或烯基，并进一步取代 C5 位上的氯（Suzuki-Miyaura 偶联或 Buchwald-Hartwig 胺化），得到 2,5,7-三取代吲哚。
We report a facile three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline, with the first step featuring Pd/dihydroxyterphenylphosphine (DHTP)-catalyzed ortho-selective Sonogashira coupling followed by cyclization to afford 2-substituted 5,7-dichloroindoles. Subsequent introduction of aryl or alkenyl groups at the C7 position was achieved by Pd/DHTP-catalyzed site-selective Kumada–Tamao–Corriu coupling, with further substitution of the chlorine at the C5 position (Suzuki–Miyaura coupling or Buchwald–Hartwig amination) affording 2,5,7-trisubstituted indoles.