Cu(BF4)2/AC-Catalyzed Synthesis of N-Substituted Anilines, N-Substituted 1,6-Naphthyridin-5(6 H)-one, and Isoquinolin-1(2 H)-one

Shuang Wu; Qiong Liu; Quanfeng Zhang; Ya Zhou; Meiyan Liu; Youlin Zeng

doi:10.1021/acsomega.2c04299

Cu(BF₄)₂/AC-Catalyzed Synthesis of N-Substituted Anilines, N-Substituted 1,6-Naphthyridin-5(6 H)-one, and Isoquinolin-1(2 H)-one

ACS Omega. 2022 Dec 7;7(50):46174-46182. doi: 10.1021/acsomega.2c04299. eCollection 2022 Dec 20.

Authors

Shuang Wu^{1

2}, Qiong Liu³, Quanfeng Zhang^{1

2}, Ya Zhou^{1

2}, Meiyan Liu^{1

2}, Youlin Zeng^{1

2}

Affiliations

¹ Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China.
² Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University, Changsha 410081, China.
³ Institute of Analysis, Guangdong Academy of Sciences (China National Analytical Center, Guangzhou), Guangzhou 510070, Guangdong, China.

Abstract

Herein, we report practical Cu(BF₄)₂/activated carbon-catalyzed amination of various anilines, isoquinolinone, and naphthyridinone with aryl boronic acids. The ultrasonic and rotary evaporation treatment of the mixture of aq. Cu(BF₄)₂ and activated carbon in methanol afforded a novel Cu(II)-catalyst, which is air-stable and can be effectively applied in the Chan-Lam coupling reaction. The products of N-arylation were isolated in good to excellent yields at low catalytic loading. And Cu(BF₄)₂/AC also showed good reusability.