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Electroredox carbene organocatalysis with iodide as promoter

Author

Listed:
  • Peng Zhou

    (Sun Yat-sen University)

  • Wenchang Li

    (Sun Yat-sen University)

  • Jianyong Lan

    (Sun Yat-sen University)

  • Tingshun Zhu

    (Sun Yat-sen University)

Abstract

Oxidative carbene organocatalysis, inspired from Vitamin B1 catalyzed oxidative activation from pyruvate to acetyl coenzyme A, have been developed as a versatile synthetic method. To date, the α-, β-, γ-, δ- and carbonyl carbons of (unsaturated)aldehydes have been successfully activated via oxidative N-heterocyclic carbene (NHC) organocatalysis. In comparison with chemical redox or photoredox methods, electroredox methods, although widely used in mechanistic study, were much less developed in NHC catalyzed organic synthesis. Herein, an iodide promoted electroredox NHC organocatalysis system was developed. This system provided general solutions for electrochemical single-electron-transfer (SET) oxidation of Breslow intermediate towards versatile transformations. Radical clock experiment and cyclic voltammetry results suggested an anodic radical coupling pathway.

Suggested Citation

  • Peng Zhou & Wenchang Li & Jianyong Lan & Tingshun Zhu, 2022. "Electroredox carbene organocatalysis with iodide as promoter," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31453-7
    DOI: 10.1038/s41467-022-31453-7
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    References listed on IDEAS

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    1. Matthew N. Hopkinson & Christian Richter & Michael Schedler & Frank Glorius, 2014. "An overview of N-heterocyclic carbenes," Nature, Nature, vol. 510(7506), pages 485-496, June.
    2. Yingguo Liu & Qiao Chen & Chengli Mou & Lutai Pan & Xiaoyong Duan & Xingkuan Chen & Hongzhong Chen & Yanli Zhao & Yunpeng Lu & Zhichao Jin & Yonggui Robin Chi, 2019. "Catalytic asymmetric acetalization of carboxylic acids for access to chiral phthalidyl ester prodrugs," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    3. Tingshun Zhu & Pengcheng Zheng & Chengli Mou & Song Yang & Bao-An Song & Yonggui Robin Chi, 2014. "Benzene construction via organocatalytic formal [3+3] cycloaddition reaction," Nature Communications, Nature, vol. 5(1), pages 1-6, December.
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    Cited by:

    1. Xuefeng Tan & Qingli Wang & Jianwei Sun, 2023. "Electricity-driven asymmetric bromocyclization enabled by chiral phosphate anion phase-transfer catalysis," Nature Communications, Nature, vol. 14(1), pages 1-9, December.

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