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Metal-Free Synthesis of Sulfones and Sulfoxides through Aldehyde-Promoted Aerobic Oxidation of Sulfides

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Abstract

Metal-free aerobic oxidation of aryl sulfides to sulfoxides and sulfones has been developed in the presence of aliphatic aldehydes with excellent selectivity and yields. The reaction proceeded under mild conditions with the catalysis of N-hydroxyphthalimide (NHPI). Control experiments indicated that the reaction underwent a free radical pathway with the acylperoxyl radicals generated from aldehydes in situ as the key intermediates. The aromatic aldehydes were less efficient in the sulfide oxidation, which might be explained by the fact that the aromatic ring dispersed the electrons of free radicals and thus weakened the attacking ability of peroxy free radicals.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 22073081), and the Fundamental Research Funds for the Central Universities. L. Wang gratefully acknowledge the financial support for this research by the Zhejiang Province Postdoctoral Science Foundation (Grant No. ZJ2020159).

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Authors and Affiliations

  1. Department of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Lingyao Wang, Jia Yao & Haoran Li

  2. State Key Laboratory of Chemical Engineering, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Yuanbin Zhang & Haoran Li

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  1. Lingyao Wang
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Correspondence to Haoran Li.

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Wang, L., Zhang, Y., Yao, J. et al. Metal-Free Synthesis of Sulfones and Sulfoxides through Aldehyde-Promoted Aerobic Oxidation of Sulfides. Catal Lett 152, 1131–1139 (2022). https://doi.org/10.1007/s10562-021-03706-5

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