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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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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DOI: https://doi.org/10.1007/s11426-022-1283-7