Modular Synthesis of <i>gem</i>-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

A novel and efficient modular synthesis of <i>gem</i>-difluorotetrahydrocarbazolone scaffolds via copper-catalyzed radical cascade cyclization of bromodifluoroacetyl indoles and olefins has been reported. This operationally simple protocol provides straightforward and practical access to a series of privileged <i>gem</i>-difluorotetrahydrocarbazolone scaffolds from readily available starting materials, with the feature of broad functional group tolerance and mild reaction conditions. Moreover, the method could be used for the late-stage functionalization of bioactive molecules, which opens up the possibility for practical applications.

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Publication Details

Journal
Organic Letters
Published
2024-10-16
DOI
https://doi.org/10.1021/acs.orglett.4c03386
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.42

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article

Modular Synthesis of gem-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

Qingyu Luo, Fei Du, Enqi Zhang, Xingxing Wu et al.
2 citations
Organic Letters
Fluorine in Organic Chemistry
0.42
article

Modular Synthesis of gem-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

Qingyu Luo, Fei Du, Enqi Zhang, Xingxing Wu, Yichen Wu, X.R. Zhuo, Wu Liang, Qianhui Yu, Bin Pan, Yu-Hang Ye
article en
2 citations

Abstract

A novel and efficient modular synthesis of <i>gem</i>-difluorotetrahydrocarbazolone scaffolds via copper-catalyzed radical cascade cyclization of bromodifluoroacetyl indoles and olefins has been reported. This operationally simple protocol provides straightforward and practical access to a series of privileged <i>gem</i>-difluorotetrahydrocarbazolone scaffolds from readily available starting materials, with the feature of broad functional group tolerance and mild reaction conditions. Moreover, the method could be used for the late-stage functionalization of bioactive molecules, which opens up the possibility for practical applications.

Organic LettersVol. 26(42)
Army Medical University (CN), Chongqing Medical University (CN)
Chongqing Medical University, Chongqing Municipal Education Commission
Openalex Percentile: Top 42%
Fluorine in Organic Chemistry
0.42
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Modular Synthesis of <i>gem</i>-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins — Qingyu Luo, Fei Du, et al. · Organic Letters (2024) | TGRS Research Map | TGRS