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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
› InstitutsangabenThis project was supported by the National Natural Science Foundation of China (21776260, 21773211 and 21773210) and the Natural Science Foundation of Zhejiang Province (LY17B060007).
Weitere Informationen

Publikationsverlauf

Received: 01. November 2019

Accepted after revision: 27. November 2019

Publikationsdatum:
16. Dezember 2019 (online)

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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.

Key words

photocatalysis - lactonization - 2-arylbenzoic acids - 2,3-dichloro-5,6-dicyano-1,4-benzoquinone - oxygen

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691537.
  • Supporting Information
 

  • References and Notes


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