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Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene

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Abstract

A novel difluorocarbene promoted single-atom skeletal editing of 2H-indazoles is demonstrated herein. Ethyl bromodifluoroacetate was severed as the difluorocarbene source in the current protocol, facilitating the cleavage of the N−N bond via carbon atom insertion. This metal-free ring expansion reaction enables the late-stage diversification of indazole skeletons, assembling a diverse array of functionalized quinazolin-4(3H)-ones in decent yields with excellent functional group compatibility.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21931013, 22271105), the Natural Science Foundation of Fujian Province (2022J02009), the Science and Technology Research Project of Education Department of Hubei Province (B2021133) and the Hubei Key Laboratory of Pollutant Analysis & Reuse Technology (PA190109).

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Authors and Affiliations

  1. Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, China

    Yao Zhou, Fuling Chen, Ziru Li, Junjie Dong, Jingnan Li & Bohao Zhang

  2. Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China

    Qiuling Song

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  1. Yao Zhou
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  2. Fuling Chen
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  3. Ziru Li
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  7. Qiuling Song
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Correspondence to Qiuling Song.

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The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Zhou, Y., Chen, F., Li, Z. et al. Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene. Sci. China Chem. 66, 1975–1981 (2023). https://doi.org/10.1007/s11426-023-1599-4

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  • DOI: https://doi.org/10.1007/s11426-023-1599-4

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