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Visible light-mediated NHCs and photoredox co-catalyzed radical 1,2-dicarbonylation of alkenes for 1,4-diketones

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Abstract

Alkenes are ubiquitous, and the difunctionalization of alkenes represents one of the most practical approaches for the construction of value-added compounds. Dicarbonylation of alkenes provides direct access to value-added 1,4-dicarbonyl compounds. However, selectivity control for unsymmetric 1,2-dicarbonylation is of great challenge. We herein describe NHCs and photocatalysis co-catalyzed three-component radical 1,2-dicarbonylation of alkenes by distinguishing two carbonyl groups, providing structurally diversified 1,4-diketones. Distinct properties of acyl radical and NHCs-stabilized ketyl radical contributed to selectivity control. Acyl radicals are rapidly added to alkenes delivering alkyl radicals, which undergo subsequent radical-radical cross-coupling with NHCs-stabilized ketyl-type radicals, affording 1,2-dicarbonylation products. This transformation features mild reaction conditions, broad substrate scope, and excellent selectivity, providing a general and practical approach for the dicarbonylation of olefins.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22001157, 21831002, 22193012), the Ten Thousand Talents Program, the Fundamental Research Funds for the Central Universities (2412022QD016, 2412021QD007), the Natural Science Foundation of Jilin Province (YDZJ202201ZYTS338) and the Natural Science Foundation of Shaanxi Province (2020JQ-404).

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Authors and Affiliations

  1. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, China

    Lihong Wang, Jiuli Xia, Mingrui Li, Ruiyang Ma, Guangfan Zheng & Qian Zhang

  2. School of Environment, Northeast Normal University, Changchun, 130117, China

    Jiaqiong Sun

  3. Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Korea

    Lianjin Zhang

  4. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China

    Qian Zhang

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  1. Lihong Wang
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  2. Jiaqiong Sun
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  3. Jiuli Xia
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  4. Mingrui Li
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  5. Lianjin Zhang
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Correspondence to Guangfan Zheng or Qian Zhang.

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Supporting information The supporting information is available online at https://chem.scichina.com and https://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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Wang, L., Sun, J., Xia, J. et al. Visible light-mediated NHCs and photoredox co-catalyzed radical 1,2-dicarbonylation of alkenes for 1,4-diketones. Sci. China Chem. 65, 1938–1944 (2022). https://doi.org/10.1007/s11426-022-1328-5

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  • DOI: https://doi.org/10.1007/s11426-022-1328-5

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