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Metal-free synthesis of nitriles from aldehydes and ammonium by visible-light photocatalysis

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Abstract

A green method for synthesis of nitriles from aldehydes and ammonium salts under air is developed under extremely mild conditions, i.e., 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a photocatalyst, 2,2,6,6-tetrametylpiperidine-1-oxyl (TEMPO) as a cocatalyst, and oxygen (ambient air) as the terminal oxidant, visible light irradiation of substrate solutions, producing the desired nitriles with excellent yields. The reaction involves two distinct transformations, imine formation between an aldehyde and an ammonium salt and photocatalytic oxidation of the formed imine by air to a nitrile.

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Acknowledgements

This work was supported by the National Key R&D Program of China (2021YFA1500100, 2022YFA1502900), the National Natural Science Foundation of China (21933007, 22193013, 22088102), the Strategic Priority Research Program of the Chinese Academy of Science (XDB17000000) and New Cornerstone Science Foundation.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Photochemical Conversion and Optoelectronic Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Xu He, Yi-Wen Zheng, Bin Chen, Ke Feng, Chen-Ho Tung & Li-Zhu Wu

  2. School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049, China

    Xu He, Bin Chen, Ke Feng, Chen-Ho Tung & Li-Zhu Wu

  3. BayRay Innovation Center, Shenzhen Bay Laboratory, Shenzhen, 518107, China

    Yi-Wen Zheng

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  1. Xu He
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Correspondence to Bin Chen or Li-Zhu Wu.

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He, X., Zheng, YW., Chen, B. et al. Metal-free synthesis of nitriles from aldehydes and ammonium by visible-light photocatalysis. Sci. China Chem. 66, 2852–2857 (2023). https://doi.org/10.1007/s11426-023-1748-4

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