hi催化烯醇与吲哚亲核试剂的分子间氢化芳基化反应以获得c3 -苄基化的吲哚衍生物

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-05-08 DOI:10.1016/j.tet.2025.134699

Bo-Yuan Zhang , Cui Yang , Xiao-Long Yuan , Sheng-Yang Xu , Luo-Xu Liang , Zi-Ya Huang , Jian-Yun Mei , Yun Zhang , Xue-Qing Mou , Yong-Zheng Chen

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引用次数: 0

摘要

描述了一种hi促进的烯醇分子间氢化芳基化反应。利用催化量的氢碘酸（水中57 wt %），各种富电子的烯醇，包括4-芳基丁-3-烯-1-醇、4-芳基-4-烯-1-醇、5-芳基己-5-烯-1-醇和5-芳基-4-烯-1-醇，在室温下与吲哚亲核试剂有效反应，得到产率中等至较高的3-苄基吲哚衍生物。机理实验表明，烯烃直接氢化芳基化和环化/亲核开环级联可能协同作用，导致反应的高效率和区域选择性。

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HI-catalyzed intermolecular hydroarylation of alkenyl alcohols with indole nucleophiles to access C3-benzylated indole derivatives

A HI-promoted intermolecular hydroarylation of alkenyl alcohols was described. Utilizing a catalytic amount of hydroiodic acid (57 wt % in H₂O), a variety of electron-rich alkenyl alcohols, including 4-arylbut-3-en-1-ols, 4-arylpent-4-en-1-ols, 5-arylhex-5-en-1-ols, and 5-arylpent-4-en-1-ols, efficiently reacted with indole nucleophiles at room temperature to afford C3-benzylated indole derivatives in moderate to good yields. Mechanism experiments suggest that both the direct alkene hydroarylation and a cyclization/nucleophilic ring-opening cascade pathway may synergistically operate, contributing to the high efficiency and regioselectivity of the reaction.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.