Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide

Teppei Sasaki, Katsuhiko Moriyama and Hideo Togo*

*Graduate School of Science and Molecular Chirality Research Center, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

T. Sasaki, K. Moriyama, H. Togo, J. Org. Chem., 2017, 82, 11727-11734.

DOI: 10.1021/acs.joc.7b01433

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Abstract

Treatment of N-tosyl-2-propynylamines with diphenyliodonium triflate in the presence of K₃PO₄ and a catalytic amount of CuCl at room temperature followed by N-iodosuccinimide and BF₃·OEt₂ at 0°C, and then NaOH in methanol solution provided 3-iodo-4-arylquinolines. Products underwent various cross-coupling reactions and were smoothly dehalogenated with zinc.

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Key Words

quinolines, NIS

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ID: J42-Y2017