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Construction of C-C bonds via photoreductive coupling of ketones and aldehydes in the metal-organic-framework MFM-300(Cr)

Author

Listed:
  • Tian Luo

    (University of Manchester)

  • Lili Li

    (University of Manchester)

  • Yinlin Chen

    (University of Manchester)

  • Jie An

    (China Agricultural University)

  • Chengcheng Liu

    (University of Manchester
    Shandong University)

  • Zheng Yan

    (University of Manchester
    Jiaxing University)

  • Joseph H. Carter

    (University of Manchester
    Harwell Science Campus)

  • Xue Han

    (University of Manchester)

  • Alena M. Sheveleva

    (University of Manchester
    University of Manchester)

  • Floriana Tuna

    (University of Manchester
    University of Manchester)

  • Eric J. L. McInnes

    (University of Manchester
    University of Manchester)

  • Chiu C. Tang

    (Harwell Science Campus)

  • Martin Schröder

    (University of Manchester)

  • Sihai Yang

    (University of Manchester)

Abstract

Construction of C-C bonds via reductive coupling of aldehydes and ketones is hindered by the highly negative reduction potential of these carbonyl substrates, particularly ketones, and this renders the formation of ketyl radicals extremely endergonic. Here, we report the efficient activation of carbonyl compounds by the formation of specific host-guest interactions in a hydroxyl-decorated porous photocatalyst. MFM-300(Cr) exhibits a band gap of 1.75 eV and shows excellent catalytic activity and stability towards the photoreductive coupling of 30 different aldehydes and ketones to the corresponding 1,2-diols at room temperature. Synchrotron X-ray diffraction and electron paramagnetic resonance spectroscopy confirm the generation of ketyl radicals via confinement within MFM-300(Cr). This protocol removes simultaneously the need for a precious metal-based photocatalyst or for amine-based sacrificial agents for the photochemical synthesis.

Suggested Citation

  • Tian Luo & Lili Li & Yinlin Chen & Jie An & Chengcheng Liu & Zheng Yan & Joseph H. Carter & Xue Han & Alena M. Sheveleva & Floriana Tuna & Eric J. L. McInnes & Chiu C. Tang & Martin Schröder & Sihai Y, 2021. "Construction of C-C bonds via photoreductive coupling of ketones and aldehydes in the metal-organic-framework MFM-300(Cr)," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23302-w
    DOI: 10.1038/s41467-021-23302-w
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    Cited by:

    1. Jia Yu & Peng Zhang & Lulu Li & Kailang Li & Gong Zhang & Jia Liu & Tuo Wang & Zhi-Jian Zhao & Jinlong Gong, 2022. "Electroreductive coupling of benzaldehyde by balancing the formation and dimerization of the ketyl intermediate," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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