One-Pot Approach to 1,2-Disubstituted Indoles via Cu(II)-Catalyzed Coupling/Cyclization under Aerobic Conditions and Its Application for the Synthesis of Polycyclic Indoles

Jilong Gao, Yingying Shao, Jiaoyan Zhu, Jiaqi Zhu, Hui Mao, Xiaoxia Wang* and Xin Lv*

*Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China, Email: wangxiaoxiazjnu.cn, lvxinzjnu.cn

J. Gao, Y. Shao, J. Zhu, H. Mao, X. Wang, X. Lv, J. Org. Chem., 2014, 79, 9000-9008.

DOI: 10.1021/jo501250u

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Abstract

A Cu(II)-catalyzed domino coupling/cyclization process under aerobic conditions enables a straightforward assembly of a wide range of 1,2-disubstituted indole derivatives from 2-alkynylanilines and boronic acids. 2-(2-Bromoaryl)-1-aryl-1H-indoles, which were selectively generated in one pot under Cu catalysis, can be converted into indolo[1,2-f]phenanthridines via a subsequent Pd-catalyzed intramolecular direct C(sp²)-H arylation.

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Key Words

indoles, Chan-Lam coupling

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ID: J42-Y2014