Construction of multifunctionalized (oxo)indoles via O-Selective interception of the zwitterionic intermediate with N=O.

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-08-05 DOI:10.1007/s11030-025-11279-3

Bao-Fan Wang, Ziming Qiu, Fei Lian, Mengke Zhang, Tai-Chen Liu, Zheng-Hui Kang, Jiu-Ling Li

引用次数: 0

Abstract

A straightforward multi-component method is developed to construct multifunctionalized (oxo)indoles under Pd(II) catalysis via intramolecular or intermolecular reaction pathways between electron-rich arenes, diazo compounds, and nitrosoarenes. Under the catalysis of palladium, metal carbene, generated from diazo compound, reacts with electron-rich arene to form zwitterionic intermediate, which is trapped by activated nitrosobenzene to give the desired product. It is worth noting that indole and nitrosobenzene have a competitive relationship and react with diazo compounds to produce different two-component products. Therefore, in multi-component reactions of diazo compounds, electron-rich arene, and nitrosobenzene, obtaining a single multifunctional indole product with high chemical selectivity remains a visible challenge.

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用N=O选择性截取两性离子中间体构建多功能化（氧）吲哚。

在Pd（II）催化下，通过富电子芳烃、重氮化合物和亚硝基芳烃之间的分子内或分子间反应途径，建立了一种简单的多组分方法来构建多功能化（氧）吲哚。重氮化合物生成的金属碳在钯的催化下与富电子芳烃反应生成两性离子中间体，被活化的亚硝基苯捕获得到所需产物。值得注意的是，吲哚和亚硝基苯具有竞争关系，并与重氮化合物反应生成不同的双组分产物。因此，在重氮化合物、富电子芳烃和亚硝基苯的多组分反应中，获得具有高化学选择性的单一多功能吲哚产物仍然是一个明显的挑战。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;