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Oxidation-induced ortho-selective C–H bond functionalization of 2-naphthylamine derivative

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Abstract

Selective C–H bond functionalization has been emerged as a versatile strategy for the construction of new chemical bonds. In the past decades, the directing group (DG)-assisted C–H bond activation has been developed as one of the most efficient methods for selective C–H functionalization. Although a great progress has been made by utilizing this traditional method, developing new strategy for selective C–H bond functionalization is still highly demanded. Hence, a novel oxidation-induced C–H bond functionalization method was demonstrated in this work. By this new method, ortho-C(sp2)–H chlorination of N-substituted 2-naphthylamine was realized in a highly selective manner.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21390402, 21520102003, 21702150), the National Basic Research Program of China (2012CB725302), the CAS Interdisciplinary Innovation Team and the Hubei Province Natural Science Foundation of China (2017CFA010), and China Postdoctoral Science Foundation (BX201600114, 2016M602340). XAS study was performed at National Synchrotron Radiation Research Center. The Program of Introducing Talents of Discipline to Universities of China is also appreciated.

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Authors and Affiliations

  1. The Institute for Advanced Studies, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China

    Dongchao Zhang, Zhiliang Huang & Aiwen Lei

  2. National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, China

    Aiwen Lei

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  1. Dongchao Zhang
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  2. Zhiliang Huang
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  3. Aiwen Lei
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Corresponding authors

Correspondence to Zhiliang Huang or Aiwen Lei.

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Dedicated to Professor Xiyan Lu on the occasion of his 90th birthday.

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Zhang, D., Huang, Z. & Lei, A. Oxidation-induced ortho-selective C–H bond functionalization of 2-naphthylamine derivative. Sci. China Chem. 61, 1274–1277 (2018). https://doi.org/10.1007/s11426-018-9218-5

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  • DOI: https://doi.org/10.1007/s11426-018-9218-5

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