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Silver-Catalyzed Intramolecular Chloroamination of Allenes: Easy Access to Functionalized 3-Pyrroline and Pyrrole Derivatives

Masahiro Sai and Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email: matsubarorgrxn.mbox.media.kyoto-u.ac.jp

M. Sai, S. Matsubara, Org. Lett., 2011, 13, 4676-4679.

DOI: 10.1021/ol201895s (free Supporting Information)


Abstract

An intramolecular chloroamination of allenes with N-chlorosuccinimide proceeds under mild conditions in the presence of a 1,10-phenanthroline-ligated cationic silver complex and 2,6-lutidine as a base. The reaction tolerates various functional groups. The chloroamination products are useful synthetic intermediates and can be easily transformed into functionalized 3-pyrroline and pyrrole derivatives.

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Key Words

3-Pyrrolines, NCS


ID: J54-Y2011-2500