Biomimetic Iron-Catalyzed Oxidation of 3-Substituted Indoles to 2-Oxindoles

Organic Letters 2026

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Authors: Changyin Zhao, Yuzhen Dong, Hongbin Liu, Jiazheng Wu, Minghui Zhu, Lei Liu, Xigong Liu
DOI: 10.1021/acs.orglett.6c00165
Cited by: 3
References: 47

Abstract

A biomimetic iron-catalyzed system has been developed for the selective oxidation of 3-substituted indoles to 3-monosubstituted 2-oxindoles using H 2 O 2 as a green oxidant under mild conditions. This catalytic approach addresses the drawbacks of stoichiometric biomimetic models and exhibits broad substrate scope and excellent functional group tolerance. Mechanistic studies suggest the reaction proceeds via an epoxide intermediate followed by a 2,3-hydride shift, with the epoxidation step being rate-determining. The method provides a sustainable route to biologically relevant 2-oxindole scaffolds.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Oxidative Organic Chemistry Reactions Metal-Catalyzed Oxygenation Mechanisms

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
7
Pages
2488–2493
Publication date
9 February 2026
Language
EN