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Updated: Feb 13, 2026
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Atomic Layer Deposition of Vanadium Dioxide and a Temperature-dependent Optical Model
Published on: May 23, 2018
12.5K
Oxidative Rearrangement of Indoles Enabled by Promiscuous Cryptic Halogenation with Vanadium-Dependent
Hyung Ji Lee1,2, Carter U Brzezinski1, Sergio A Solis1
1Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.
ACS Catalysis
|February 12, 2026
Summary
This study introduces a green biocatalytic method for synthesizing 2-oxindoles from indoles using vanadium-dependent haloperoxidases (VHPOs) and halide recycling. This approach avoids harmful waste and broadens substrate scope for valuable chemical compounds.
Area of Science:
- Organic Chemistry
- Biocatalysis
- Green Chemistry
Background:
- 2-Oxindoles are crucial scaffolds in natural products and pharmaceuticals.
- Current synthesis methods for 2-oxindoles involve harsh chemical oxidants or limited biocatalytic options.
Purpose of the Study:
- To develop a general and sustainable biocatalytic platform for indole oxidation to 2-oxindoles.
- To overcome limitations of existing chemical and enzymatic methods.
Main Methods:
- Utilized vanadium-dependent haloperoxidases (VHPOs) for oxidative rearrangement of indoles.
- Implemented enzymatic halide recycling with hydrogen peroxide as the terminal oxidant.
- Developed a catalytic system using a halide salt.
Main Results:
- Achieved efficient oxidative rearrangement of indoles to 2-oxindoles and 2-spirooxindoles.
- Demonstrated the system's effectiveness in multienzymatic and chemoenzymatic synthesis.
- Successfully applied the protocol for late-stage functionalization and gram-scale synthesis of natural products.
Conclusions:
- The developed VHPO-based system offers a versatile and environmentally friendly approach for 2-oxindole synthesis.
- This platform enables broad applications in complex molecule synthesis and drug discovery.
- The method provides a sustainable alternative to traditional chemical oxidation processes.
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