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

Xinyuan Zhang; Yufang Sun; Yujie Qu; Shengxing Xie; Fuchun Yang; Chengyu Wang; Jiawen Du; Xiaofeng Zhu; Lingkai Kong; Neng-Fei Wang

doi:10.1039/D5OB01449B

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

Xinyuan Zhang,†^a Yufang Sun,†^b Yujie Qu,^a Shengxing Xie,^a Fuchun Yang,^a Chengyu Wang,

^a Jiawen Du,^a Xiaofeng Zhu,^a Lingkai Kong

*^a and Neng-Fei Wang*^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, Linyi University, Linyi, Shandong 276000, China
E-mail: konglingkai0624@163.com, wangnengfei@lyu.edu.cn

^b State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China

Abstract

An environmentally friendly and green transition-metal–free TBAI-catalyzed C–O coupling reaction mediated by C_(sp3)–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 Chemistry

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

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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

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