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Hydrofunctionalization of Olefins to Higher Aliphatic Alcohols via Visible-Light Photocatalytic Coupling

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Abstract

An atomically economical green protocol for the hydrofunctionalization of olefins to higher aliphatic alcohols with 100% anti-Markovnikov regioselectivity was developed via visible-light photocatalytic coupling. This method employs cheap, readily available and abundant methanol as both the C1 feedstock and the hydrogen source under visible light irradiation over CdS photocatalyst. A wide scope of olefin substrates could be hydrofunctionalized successfully to the corresponding higher alcohols with high selectivity. Besides alcohol, acetone and acetonitrile can also couple with olefins to generate the corresponding hydrofunctionalization products, suggesting promising potential industrial application.

Graphical Abstract

Hydrofunctionalization of olefins to value-added chemicals with high selectivity was achieved via visible-light photocatalytic cross-coupling.

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Acknowledgements

This work was supported by Natural Science Foundation of China (21573271, 91545112 and 21703278), the National Key R&D Program of China (2017YFB0602202, 2018YFB0604700), Key Research Program of Frontier Sciences, CAS (Grant No. QYZDB-SSW-SLH035), the “Transformational Technologies for Clean Energy and Demonstration”, Strategic Priority Research Program of CAS (Grant No. XDA21020600) and the Youth Innovation Promotion Association of CAS.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shanghai University, Shanghai, 200444, China

    Jingxian Bao

  2. Key Laboratory of Low-Carbon Conversion Science and Engineering, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai, 201203, China

    Jingxian Bao, Yonghui Fan, Shuyi Zhang, Liangshu Zhong & Yuhan Sun

  3. University of the Chinese Academy of Sciences, Beijing, 100049, China

    Shuyi Zhang

  4. School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210, China

    Liangshu Zhong & Yuhan Sun

  5. Shanghai University, Shanghai, 200444, China

    Minghong Wu

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  1. Jingxian Bao
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  2. Yonghui Fan
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  4. Liangshu Zhong
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  5. Minghong Wu
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Correspondence to Liangshu Zhong or Yuhan Sun.

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Bao, J., Fan, Y., Zhang, S. et al. Hydrofunctionalization of Olefins to Higher Aliphatic Alcohols via Visible-Light Photocatalytic Coupling. Catal Lett 149, 1651–1659 (2019). https://doi.org/10.1007/s10562-019-02737-3

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  • DOI: https://doi.org/10.1007/s10562-019-02737-3

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