有机碘催化分子内 C-N 键氧化偶联合成 3-单取代羰基吲哚

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-14 DOI:10.1002/ejoc.202400822

Yang Wang, Jiang-Ning Yu, Yue Wang, Ji-Chen Yin

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引用次数: 0

摘要

介绍了一种高效的有机碘催化分子内直接 C-N 键氧化偶联反应。在一个复杂的氧化体系中迅速获得了结构多样的 3-（单）取代吲哚，收率高达 87%。各种 N-烷氧基-2-苯基丙酰胺的耐受性良好。这项研究表明，反应物芳香环上的电子效应对环化产物的选择性（C-N/C-O）有至关重要的影响。此外，3-（单）取代吲哚衍生物的克级合成和后期修饰揭示了这种转化的实际应用。

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Organoiodine Catalysed Intramolecular C−N bond Oxidative Coupling for the Synthesis of 3-Monosubstituted Oxindoles

An efficient organoiodine-catalysed intramolecular direct C–N bond oxidative coupling reaction is presented. Structurally diverse 3-(mono)substituted oxindoles were rapidly obtained in a complex oxidative system in up to 87% yield. Various N-alkoxy-2-phenylpropanamides were well-tolerated. This study showed that the electronic effects on the aromatic ring of reactants have a crucial effect on the selectivity (C−N/C−O) of cyclisation products. In addition, gram-scale synthesis and late-stage modification of 3-(mono)substituted oxindole derivatives revealed the practical application of this transformation.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.