Selective Halogen-Magnesium Exchange Reaction via Organomagnesium Ate Complex

Atsushi Inoue, Kazuya Kitagawa, Hiroshi Shinokubo and Koichiro Oshima*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University,Yoshida, Sakyo-ku, Kyoto 606-8501, Japan

A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, J. Org. Chem., 2001, 66, 4333-4339.

DOI: 10.1021/jo015597v

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Abstract

Tributylmagnesate (ⁿBu₃MgLi) and the more reactive dibutylisopropylmagnesate (ⁱPrⁿBu₂MgLi) induce facile iodine/bromine-magnesium exchange to provide various polyfunctionalized arylmagnesium species. The exchange of alkenyl halides using this method proceeds with retention of configuration of the double bond.

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Key Words

benzylic alcohols, allylation of arenes, allylic alcohols, 1,4-dienes

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ID: J42-Y2001