RhodiumIII/SilverI Relay Catalyzed C—H Aminomethylation with Imine Equivalents and Lewis Acid Catalyzed [4+2] Cycloaddition of Indoles with Triarylhexahydrotriazine†,Chinese Journal of Chemistry

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RhodiumIII/SilverI Relay Catalyzed C—H Aminomethylation with Imine Equivalents and Lewis Acid Catalyzed [4+2] Cycloaddition of Indoles with Triarylhexahydrotriazine†
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-03-26 , DOI: 10.1002/cjoc.202000018
Ruixing Liu ₁ , Yin Wei ₁ , Min Shi ₁

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A Rh^III/Ag^I relay‐catalyzed C(sp²)—H coupling of indoles with triarylhexahydrotriazine (THT) is reported in this context. Upon merging Rh^III‐catalyzed C(sp²)—H bond activation and silver promoted THT dissociation, an efficient indole's C3 aminomethylation protocol is uncovered, providing C3 aminomethyl indoles in good yields and exhibiting potential applications for the synthesis of complicated bioactive compounds. We revealed the C3‐selectivity of this reaction through a detailed mechanistic investigation. Meanwhile, during the examination of the reaction conditions, we discovered another [4+2] cycloaddition pathway to afford tetrahydro‐indolo[3,2‐c]quinoline scaffold products via silver or Lewis acid catalysis.

中文翻译：

铑III /银I中继与亚胺当量催化CH氨基甲基化，路易斯酸与三芳基六氢三嗪催化吲哚的[4 + 2]环加成反应†

本文报道了Rh ^III / Ag ^I中继催化吲哚与三芳基六氢三嗪（THT）的C（sp ²）-H偶联。合并Rh ^III催化的C（sp ²）-H键活化和银促进的THT解离后，便发现了有效的吲哚的C3氨基甲基化方案，可提供高收率的C3氨基甲基吲哚，并显示出用于合成复杂生物活性化合物的潜在应用。我们通过详细的机理研究揭示了该反应的C3选择性。同时，在检查反应条件期间，我们发现了另一种[4 + 2]环加成途径，可提供四氢-吲哚[3,2- c ]喹啉支架产品通过银或路易斯酸催化。

更新日期：2020-03-26

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