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A visible-light-photocatalytic water-splitting strategy for sustainable hydrogenation/deuteration of aryl chlorides

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Abstract

Hydrogenation/deuteration of carbon chloride (C−Cl) bonds is of high significance but remains a remarkable challenge in synthetic chemistry, especially using safe and inexpensive hydrogen donors. In this article, a visible-light-photocatalytic watersplitting hydrogenation technology (WSHT) is proposed to in-situ generate active H-species (i.e., Had) for controllable hydrogenation of aryl chlorides instead of using flammable H2. When applying heavy water-splitting systems, we could selectively install deuterium at the C−Cl position of aryl chlorides under mild conditions for the sustainable synthesis of high-valued added deuterated chemicals. Sub-micrometer Pd nanosheets (Pd NSs) decorated crystallined polymeric carbon nitrides (CPCN) is developed as the bifunctional photocatalyst, whereas Pd NSs not only serve as a cocatalyst of CPCN to generate and stabilize H (D)-species but also play a significant role in the sequential activation and hydrogenation/deuteration of C−Cl bonds. This article highlights a photocatalytic-WSHT for controllable hydrogenation/deuteration of low-cost aryl chlorides, providing a promising way for the photosynthesis of high-valued added chemicals instead of the hydrogen evolution.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21972094, 51701127, 21401190), China Postdoctoral Science Foundation (2017M612709), Guangdong Special Support Program, Pengcheng Scholar Program, Shenzhen Peacock Plan (KQJSCX20170727100802505, KQTD2016053112042971), Educational Commission of Guangdong Province (2016KTSCX126), Foundation for Distinguished Young Talents in Higher Education of Guangdong (2018KQNCX221), Shenzhen Innovation Program (JCYJ 20170818142642395). We are thankful for the support of TEM characterizations from the Electron Microscopy Center of Shenzhen University and computational source supplied by the National Supercomputing Center in Shenzhen (Shenzhen Cloud Computing Center).

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Authors and Affiliations

  1. International Collaborative Laboratory of 2D Materials for Optoelectronic Science & Technology, Engineering Technology Research Center for 2D Materials Information Functional Devices and Systems of Guangdong Province, Institute of Microscale Optoeletronics, , Shenzhen University, Shenzhen, 518060, China

    Xiang Ling, Yangsen Xu, Chuntian Qiu, Guoqiang Zhang & Chenliang Su

  2. School of Pharmacy; Key Laboratory of Resource Biology and Biotechnology in Western China (Northwest University), Ministry of Education; Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi’an, 710069, China

    Shaoping Wu & Mofan Liu

  3. Yunnan Key Laboratory for Micro/nano Materials & Technology, the School of Materials Science and Engineering, Yunnan University, Kunming, 650000, China

    Peng Yang

  4. College of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing, 314001, China

    Hongwei Zhou

Authors
  1. Xiang Ling
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  2. Yangsen Xu
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  3. Shaoping Wu
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  4. Mofan Liu
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  5. Peng Yang
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  6. Chuntian Qiu
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  7. Guoqiang Zhang
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  8. Hongwei Zhou
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  9. Chenliang Su
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Correspondence to Chenliang Su.

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Ling, X., Xu, Y., Wu, S. et al. A visible-light-photocatalytic water-splitting strategy for sustainable hydrogenation/deuteration of aryl chlorides. Sci. China Chem. 63, 386–392 (2020). https://doi.org/10.1007/s11426-019-9672-8

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