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Catalytic chemodivergent annulations between α-diketones and alkynyl α-diketones

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Abstract

Four types of unprecedented and chemodivergent reactions between α-diketones and alkynyl α-diketones have been achieved under the catalysis of phosphine and Brønsted base, respectively, leading to the rapid construction of four different classes of biologically important but synthetically challenging molecular scaffolds including 2-hydroxyfuran-3(2H)-ones, 4-hydroxy-2-oxabicyclo[2.2.1]heptan-3-ones, 1,3-diaryl cyclobutanes, and 4-(furan-2(3H)-ylidene)cyclopent-2-enones. The formation of the products includes two novel rearrangement processes, and further transformations on the products can be easily achieved to deliver value-added substances such as highly functionalized cyclopentanes. Moreover, the 2-hydroxyfuran-3(2H)-one products display promising photophysical properties such as green luminescence under UV light and aggregation-induced emission effect, showing the practical application value of this work. The great potential of α-diketones in both synthetic chemistry and material science has been unambiguously demonstrated.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21871260, 22071242), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000), Fujian Natural Science Foundation (2018J05035), the China Postdoctoral Science Foundation (2018M630734) and the Science and Technology Research Program of the Education Department of Jiangxi Province (GJJ1991151).

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Authors and Affiliations

  1. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350100, China

    Xiangwen Kong, Fang Yu, Zhizhou Chen, Fan Gong, Shuang Yang & Xinqiang Fang

  2. Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350100, China

    Xinqiang Fang

  3. Orthopedics Department, Guangdong Provincial Hospital of Traditional Chinese Medicine, The Second Affiliated Hospital of Guangzhou University of Chinese Medicine, Guangzhou, 510120, China

    Jinggong Liu

  4. Pingxiang University, Pingxiang, 337055, China

    Benlong Luo

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  1. Xiangwen Kong
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Correspondence to Xinqiang Fang.

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Kong, X., Yu, F., Chen, Z. et al. Catalytic chemodivergent annulations between α-diketones and alkynyl α-diketones. Sci. China Chem. 64, 991–998 (2021). https://doi.org/10.1007/s11426-021-9972-3

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