Pd/Et3N·HI-Catalyzed Intramolecular C–H Alkylation to Access [a]-Annulated Indoles via Highly Regioselective Ring-Opening of Epoxides,The Journal of Organic Chemistry

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Pd/Et3N·HI-Catalyzed Intramolecular C–H Alkylation to Access [a]-Annulated Indoles via Highly Regioselective Ring-Opening of Epoxides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-07 , DOI: 10.1021/acs.joc.2c00630
Xu Dong ₁ , Xi Sun ₁ , Yi Yang ₁ , Weiwei Liu ₁ , Bowen Zheng ₁ , Xinjin Li ₁ , Daopeng Zhang ₁ , Fagang Wang ₁ , Hui Liu ₁

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A Pd/Et₃N·HI-catalyzed intramolecular C–H alkylation of indoles with epoxides was achieved to furnish N-fused indole frameworks (5-, 6-, and 7-membered rings) bearing an alcohol group. The conversion proceeded smoothly in the presence of a catalytic amount of Et₃N·HI together with a palladium catalyst and exhibited great functional group tolerance. The employment of Et₃N·HI not only avoids the prior preparation of alkyl halide substrates but also is the key to the high chemoselective ring-opening of epoxides. Preliminary mechanism explorations strongly support a radical pathway, and the catalytic cycle was established tentatively according to the mechanism investigation experiments.

中文翻译：

Pd/Et3N·HI催化分子内C-H烷基化通过环氧化物的高区域选择性开环获得[a]-环状吲哚

实现了 Pd/Et ₃ N·HI 催化的吲哚与环氧化物的分子内 C-H 烷基化，以提供带有醇基的N-稠合吲哚骨架（5-、6-和 7-元环）。_{在催化量的Et 3} N·HI 和钯催化剂的存在下，转化过程顺利进行，并表现出很好的官能团耐受性。Et ₃ N·HI的使用不仅避免了卤代烷底物的前期制备，而且是环氧化物高化学选择性开环的关键。初步机理探索强烈支持自由基途径，根据机理研究实验初步建立了催化循环。

更新日期：2022-06-07

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