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Iron-Catalyzed Arylmagnesiation of Aryl(alkyl)acetylenes in the Presence of an N-Heterocyclic Carbene Ligand

Takafumi Yamagami, Ryo Shintani, Eiji Shirakawa,* and Tamio Hayashi*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan1, Email: thayashikuchem.kyoto-u.ac.jp, shirakawakuchem.kyoto-u.ac.jp

T. Yamagami, R. Shintani, E. Shirakawa, T. Hayashi, Org. Lett., 2007, 9, 1045-1048.

DOI: 10.1021/ol063132r (free Supporting Information)


Abstract

Addition of arylmagnesium bromides to aryl(alkyl)acetylenes gave high yields of the corresponding alkenylmagnesium reagents in the presence of an iron catalyst and a N-heterocyclic carbene ligand. Subsequent treatment with electrophiles allows the formation of tetrasubstituted alkenes.

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Key Words

Arenes, Kumada Coupling


ID: J54-Y2007-0900