Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o -Allenyl Anilines
Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o -Allenyl Anilines
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通过邻联烯基苯胺的分子内氨基羟基化氧化为吲哚的路线
DOI：
10.1021/acs.joc.1c01379
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Njardarson, Jon T.
中科院分区：
文献类型：
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作者：
Lauta, Nicholas R.;Williams, Ryan E.;Smith, David T.;Kumirov, Vlad K.;Njardarson, Jon T.
报道了一种新的邻丙二烯基苯胺分子内氧化氨羟化反应。在室温下，在二氯甲烷中用羧酸铅（IV）处理氨基甲酸酯保护的苯胺导致容易的串联C-N（丙二烯环化）和C-O键形成（羧酸根捕获）以形成吲哚产物。详细的反应范围，机理和动力学研究表明，反应途径包括一个初始的Wessely脱芳构化步骤，然后环化和rearomatization。
A new intramolecular oxidative amino-hydroxylation ofo-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C–N (allene cyclization) and C–O bond formation (carboxylate trapping) to form indole products. Detailed reaction scope, mechanistic and kinetic studies suggest a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization.