TBAI-catalyzed C–H bond activation to construct the C <sub>(sp3)</sub> –O bond in water: synthesis of indole-3-carboxylic-α-esters under metal-free conditions

An environmentally friendly and green transition-metal-free TBAI-catalyzed C-O coupling reaction mediated by C<sub>(sp3)</sub>-H activation was developed to construct indole-3-carboxylic-α-esters in water. This reaction exhibited a broad substrate scope and good functional group tolerance. Remarkably, a gram-scale reaction and late-stage functionalization of many carboxylic acid drugs were smoothly achieved under the mild conditions.

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Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01449b
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

TBAI-catalyzed C–H bond activation to construct the C (sp3) –O bond in water: synthesis of indole-3-carboxylic-α-esters under metal-free conditions

Xiaofeng Zhu, Xinyuan Zhang, Lingkai Kong, Sishen Xie et al.
Organic & Biomolecular Chemistry
Catalytic C–H Functionalization Methods
article

TBAI-catalyzed C–H bond activation to construct the C (sp3) –O bond in water: synthesis of indole-3-carboxylic-α-esters under metal-free conditions

Xiaofeng Zhu, Xinyuan Zhang, Lingkai Kong, Sishen Xie, N.-L. Wang, Chengyu Wang, Yufang Sun, Fuchun Yang, Yuan Qu, Jiawen Du
article en

Abstract

An environmentally friendly and green transition-metal-free TBAI-catalyzed C-O coupling reaction mediated by C<sub>(sp3)</sub>-H activation was developed to construct indole-3-carboxylic-α-esters in water. This reaction exhibited a broad substrate scope and good functional group tolerance. Remarkably, a gram-scale reaction and late-stage functionalization of many carboxylic acid drugs were smoothly achieved under the mild conditions.

Organic & Biomolecular ChemistryVol. 23(47)
Linyi University (CN), Peking University (CN)
Openalex Percentile: Top 75%
Catalytic C–H Functionalization Methods
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