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Visible light-driven C−H activation and C–C coupling of methanol into ethylene glycol

Author

Listed:
  • Shunji Xie

    (Xiamen University)

  • Zebin Shen

    (Xiamen University)

  • Jiao Deng

    (Chinese Academy of Sciences)

  • Pu Guo

    (Xiamen University)

  • Qinghong Zhang

    (Xiamen University)

  • Haikun Zhang

    (Xiamen University)

  • Chao Ma

    (Hunan University)

  • Zheng Jiang

    (Chinese Academy of Sciences)

  • Jun Cheng

    (Xiamen University)

  • Dehui Deng

    (Chinese Academy of Sciences)

  • Ye Wang

    (Xiamen University)

Abstract

The development of new methods for the direct transformation of methanol into two or multi-carbon compounds via controlled carbon–carbon coupling is a highly attractive but challenging goal. Here, we report the first visible-light-driven dehydrogenative coupling of methanol into ethylene glycol, an important chemical currently produced from petroleum. Ethylene glycol is formed with 90% selectivity and high efficiency, together with hydrogen over a molybdenum disulfide nanofoam-modified cadmium sulfide nanorod catalyst. Mechanistic studies reveal a preferential activation of C−H bond instead of O−H bond in methanol by photoexcited holes on CdS via a concerted proton–electron transfer mechanism, forming a hydroxymethyl radical (⋅CH2OH) that can readily desorb from catalyst surfaces for subsequent coupling. This work not only offers an alternative nonpetroleum route for the synthesis of EG but also presents a unique visible-light-driven catalytic C−H activation with the hydroxyl group in the same molecule keeping intact.

Suggested Citation

  • Shunji Xie & Zebin Shen & Jiao Deng & Pu Guo & Qinghong Zhang & Haikun Zhang & Chao Ma & Zheng Jiang & Jun Cheng & Dehui Deng & Ye Wang, 2018. "Visible light-driven C−H activation and C–C coupling of methanol into ethylene glycol," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-03543-y
    DOI: 10.1038/s41467-018-03543-y
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    Cited by:

    1. 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.
    2. Chunyang Dong & Yinghao Wang & Ziqi Deng & Wenchao Wang & Maya Marinova & Karima Tayeb & Jean-Charles Morin & Melanie Dubois & Martine Trentesaux & Yury G. Kolyagin & My Nghe Tran & Vlad Martin-Diacon, 2024. "Photocatalytic dihydroxylation of light olefins to glycols by water," Nature Communications, Nature, vol. 15(1), pages 1-12, December.

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