Boron-Mediated C1-Hydroxylation of Carbazoles Using Benzoyl as the Traceless Directing Group

Herein, a metal-free BBr<sub>3</sub>-mediated C-H hydroxylation of carbazoles using benzoyl as a traceless directing group has been reported. This protocol features high efficiency and operational simplicity, offering the valuable 1-hydroxycarbazoles in moderate to excellent yields with scale-up ability under mild conditions. In addition, this transformation can be performed in one-pot, which is highlighted by the utility for the total synthesis of carbazole alkaloid murrayaquinone A.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-02-16
DOI
https://doi.org/10.1021/acs.joc.5c02691
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Boron-Mediated C1-Hydroxylation of Carbazoles Using Benzoyl as the Traceless Directing Group

Miao Tian, Kai Sun, Zexuan Zhang, Jianfeng Tao et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Boron-Mediated C1-Hydroxylation of Carbazoles Using Benzoyl as the Traceless Directing Group

Miao Tian, Kai Sun, Zexuan Zhang, Jianfeng Tao, Huiwen Zheng, Na Xie, Tao Zhou, Minghan Li, Zixian Wei
article en

Abstract

Herein, a metal-free BBr<sub>3</sub>-mediated C-H hydroxylation of carbazoles using benzoyl as a traceless directing group has been reported. This protocol features high efficiency and operational simplicity, offering the valuable 1-hydroxycarbazoles in moderate to excellent yields with scale-up ability under mild conditions. In addition, this transformation can be performed in one-pot, which is highlighted by the utility for the total synthesis of carbazole alkaloid murrayaquinone A.

The Journal of Organic ChemistryVol. 91(8)
Yantai University (CN), State Key Laboratory of Pollution Control and Resource Reuse (CN), Nanchang Hangkong University (CN)
Openalex Percentile: Top 52%
Catalytic C–H Functionalization Methods
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