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

Authors

  • 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

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)


Graphical Abstract

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