Visible-Light-Induced Arene C(sp²)-H Lactonization Promoted by DDQ and tert-Butyl Nitrite

Yiqing Wang, Shengpeng Wang, Bajin Chen, Meichao Li*, Xinquan Hu, Baoxiang Hu, Liqun Jin, Nan Sun, Zhenlu Shen*

*College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China, Email: limczjut.edu.cn, zhenlushenzjut.edu.cn

Y. Wang, S. Wang, B. Chen, M. Li, X. Hu, B. Hu, L. Jin, N. Sun, Z. Shen, Synlett, 2020, 31, 261-266.

DOI: 10.1055/s-0039-1691537

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Abstract

A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp²)-H bonds provides benzocoumarin derivatives in good yields in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and tert-butyl nitrite. This atom economic method offers mild reaction conditions, use of a green oxidant and metal-free catalysis.

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Key Words

photocatalysis, lactonization, 2-arylbenzoic acids, benzo-fused O-heterocycles, organocatalysis, photochemistry, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, oxygen

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ID: J72-Y2020