Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

Duyi Shen*, Hongyan Wang, Yanan Zheng, Xinjing Zhu, Peiwei Gong, Bin Wang, Jinmao You, Yulei Zhao* and Mianran Chao*

*School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. China, Email: shendyqfnu.edu.cn, zhaoyulei86126.com, chaomrqfnu.edu.cn

D. Shen, H. Wang, Y. Zheng, X. Zhu, P. Gong, B. Wang, J. You. Y. Zhao, M. Chao, J. Org. Chem., 2021, 86, 5354-5361.

DOI: 10.1021/acs.joc.0c03010

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Abstract

The combination of potassium persulfate and ambient air enables a catalyst- and transition-metal-free oxidation of various internal alkynes to the corresponding 1,2-diketones in very good yields. Mechanistic studies indicate a radical process with both the persulfate salt and molecular oxygen as source of the incorporated oxygen atoms.

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proposed mechanism

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Key Words

1,2-diketones, potassium peroxydisulfate, air

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ID: J42-Y2021