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Oxidative lactonization of C(sp3)-H bond in methyl aromatic alcohols enabled by proton-coupled electron transfer

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Abstract

Direct functionalization of inert C(sp3)-H bonds in pharmaceutically significant compounds is very important in modern synthetic organic chemistry. In this article, we disclose a practical and efficient method for the oxidative lactonization of benzylic C(sp3)-H bonds enabled by the synergistic interactions of organic dye-type rose bengal, n-Bu4N·Br, O2 and Na2HPO4 under visible light irradiation. This reaction does not require transition metal catalysts or strong oxidants. A range of structurally diverse phthalides has been synthesized with excellent selectivity and high functional group compatibility. The late-stage application of this reaction to the preparation of structurally complex phthalides demonstrates its synthetic utility.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21502086), the Natural Science Foundation of Fujian Province (2019J01744), the Key Project of Foundation of Fujian Province (2020J02044) and the Natural Science Foundation of Zhangzhou City (ZZ2021J13).

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Authors and Affiliations

  1. Fujian Provincial Key Laboratory of Modern Analytical Science and Separation Technology, School of Chemistry, Chemical Engineering and Environment, Minnan Normal University, Zhangzhou, 363000, China

    Shanyi Chen, Qihong Lai, Chao Liu, Hui Liu, Mingqiang Huang & Shunyou Cai

  2. Guangdong Provincial Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, 518055, China

    Shunyou Cai

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  1. Shanyi Chen
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  2. Qihong Lai
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  3. Chao Liu
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  4. Hui Liu
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Correspondence to Shunyou Cai.

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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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Chen, S., Lai, Q., Liu, C. et al. Oxidative lactonization of C(sp3)-H bond in methyl aromatic alcohols enabled by proton-coupled electron transfer. Sci. China Chem. 65, 1526–1531 (2022). https://doi.org/10.1007/s11426-022-1283-7

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