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Palladium-Catalyzed Synthesis of Indoles and Isoquinolines with in Situ Generated Phosphinimine

Qi Zhou, Zhikun Zhang, Yujing Zhou, Shichao Li, Yan Zhang and Jianbo Wang*

*Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China, Email: wangjbpku.edu.cn

Q. Zhou, Z. Zhang, Y. Zhou, S. Li, Y. Zhang, J. Wang, J. Org. Chem., 2017, 82, 48-56.

DOI: 10.1021/acs.joc.6b01864 (free Supporting Information)


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Abstract

A palladium-catalyzed coupling of aryl bromides with 2-alkynyl arylazides or 2-alkynyl benzylazides provides straightforward access to indoles and isoquinolines with high efficiency and excellent functional group compatibility. In the cyclization process, an in situ generated iminophosphorane serves as the nucleophile that attacks the alkyne moiety.


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proposed mechanism



Key Words

indoles


ID: J42-Y2017