未活化烯烃的化学选择性自由基级联极性错配硅烷芳香化反应

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-09-30 DOI:10.1039/D4QO01461H

Liang Liu, Xiao Yang, Jinghui Tong, Huajie Zhu, Lu Ouyang, Renshi Luo and Jianhua Liao

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引用次数: 0

摘要

在此，我们报告了一种实用的方法，利用烯基吲哚和容易获得的硅烷，通过自由基级联环化，选择性地获得硅烷化的吡咯并[1,2-a]吲哚。该反应是通过亲核硅烷自由基与富含 e 的烯 SOMOphiles 在配位辅助作用下发生不寻常的分子间极性错配加成反应而进行的。本文介绍了该方案的范围、官能团兼容性以及详细的机理研究。

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A chemoselective radical cascade polarity-mismatched silylarylation of unactivated alkenes†

Here, we report a practical method to selectively access silylated pyrrolo[1,2-a]indoles using alkenyl indoles and readily available silanes through a radical cascade cyclization. The reaction proceeds through an unusual intermolecular polarity-mismatched addition of a nucleophilic silyl radical to e-rich alkene SOMOphiles via a coordination-assisted interaction. The scope and functional group compatibility of the protocol as well as a detailed mechanistic investigation are presented.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.