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Dichloromethylation of enones by carbon nitride photocatalysis

Author

Listed:
  • Stefano Mazzanti

    (Max Planck Institute of Colloids and Interfaces)

  • Bogdan Kurpil

    (Max Planck Institute of Colloids and Interfaces)

  • Bartholomäus Pieber

    (Max Planck Institute of Colloids and Interfaces)

  • Markus Antonietti

    (Max Planck Institute of Colloids and Interfaces)

  • Aleksandr Savateev

    (Max Planck Institute of Colloids and Interfaces)

Abstract

Small organic radicals are ubiquitous intermediates in photocatalysis and are used in organic synthesis to install functional groups and to tune electronic properties and pharmacokinetic parameters of the final molecule. Development of new methods to generate small organic radicals with added functionality can further extend the utility of photocatalysis for synthetic needs. Herein, we present a method to generate dichloromethyl radicals from chloroform using a heterogeneous potassium poly(heptazine imide) (K-PHI) photocatalyst under visible light irradiation for C1-extension of the enone backbone. The method is applied on 15 enones, with γ,γ-dichloroketones yields of 18–89%. Due to negative zeta-potential (−40 mV) and small particle size (100 nm) K-PHI suspension is used in quasi-homogeneous flow-photoreactor increasing the productivity by 19 times compared to the batch approach. The resulting γ,γ-dichloroketones, are used as bifunctional building blocks to access value-added organic compounds such as substituted furans and pyrroles.

Suggested Citation

  • Stefano Mazzanti & Bogdan Kurpil & Bartholomäus Pieber & Markus Antonietti & Aleksandr Savateev, 2020. "Dichloromethylation of enones by carbon nitride photocatalysis," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-15131-0
    DOI: 10.1038/s41467-020-15131-0
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    Cited by:

    1. Oleksandr Savateev & Karlo Nolkemper & Thomas D. Kühne & Vitaliy Shvalagin & Yevheniia Markushyna & Markus Antonietti, 2023. "Extent of carbon nitride photocharging controls energetics of hydrogen transfer in photochemical cascade processes," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    2. Xinzhe Tian & Yinggang Guo & Wankai An & Yun-Lai Ren & Yuchen Qin & Caoyuan Niu & Xin Zheng, 2022. "Coupling photocatalytic water oxidation with reductive transformations of organic molecules," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    3. Mingcheng Yang & Ronghong Lian & Xirui Zhang & Chong Wang & Jiajia Cheng & Xinchen Wang, 2022. "Photocatalytic cyclization of nitrogen-centered radicals with carbon nitride through promoting substrate/catalyst interaction," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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