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Palladium-Catalyzed Difunctionalization of Alkynes via C-N and S-N Cleavages: A Versatile Approach to Highly Functional Indoles

Fei Zhao, Dengyou Zhang, Yong Nian, Lei Zhang, Wei Yang and Hong Liu*

*State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China, Email: hliumail.shcnc.ac.cn

F. Zhao, D. Zhang, Y. Nian, L. Zhang, W. Yang, H. Liu, Org. Lett., 2014, 16, 5124-5127.

DOI: 10.1021/ol5024745 (free Supporting Information)


Abstract

In a palladium-catalyzed intramolecular addition of C-N and S-N bond to alkynes, a wide range of functional groups including acyl, pyruvoyl, amide, and sulfonyl groups can migrate smoothly and be conveniently introduced at the C-3 position of indoles. The operational simplicity and broad substrate scope demonstrate the great potential of this method for the synthesis of highly substituted indoles.

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Key Words

indoles


ID: J54-Y2014