Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

Yufeng Wu, Guangli Zhou, Qingwei Meng*, Xiaofei Tang, Guangzhi Liu, Hang Yin, Jingnan Zhao, Fan Yang, Zongyi Yu, Yi Luo*

*State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China, Email: mengqwdlut.edu.cn, luoyidlut.edu.cn

Y. Wu, G. Zhou, Q. Meng, X. Tang, G. Liu, H. Yin, J. Zhao, F. Yang, Z. Yu, Y. Luo, J. Org. Chem., 2018, 83, 13051-13062.

DOI: 10.1021/acs.joc.8b01710

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Abstract

An aerobic photoepoxidation of α,β-unsaturated ketones is driven by visible light in the presence of tetramethylguanidine (TMG), tetraphenylporphine (H₂TPP), and molecular oxygen under mild conditions to provide α,β-epoxy ketones in good yields in 96 h. The reaction time can be shortened to 5 h using flow synthesis.

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Key Words

epoxides, oxygen, photochemistry

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ID: J42-Y2018