Synlett 2020; 31(03): 261-266
DOI: 10.1055/s-0039-1691537
letter
© Georg Thieme Verlag Stuttgart · New York

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

Yiqing Wang
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Shengpeng Wang
b   Transfar Zhilian Co., Ltd., Xiaoshan Economy & Technology Development Zone, Hangzhou 311215, P. R. of China
,
Bajin Chen
b   Transfar Zhilian Co., Ltd., Xiaoshan Economy & Technology Development Zone, Hangzhou 311215, P. R. of China
,
Meichao Li
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Xinquan Hu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Baoxiang Hu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Liqun Jin
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Nan Sun
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Zhenlu Shen
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
› Author Affiliations
This project was supported by the National Natural Science Foundation of China (21776260, 21773211 and 21773210) and the Natural Science Foundation of Zhejiang Province (LY17B060007).
Further Information

Publication History

Received: 01 November 2019

Accepted after revision: 27 November 2019

Publication Date:
16 December 2019 (online)


Abstract

A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp2)–H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.

Supporting Information

 
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