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Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents

Kaori Ando*, Takahisa Kobayashi and Nariaki Uchida

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan, Email: andogifu-u.ac.jp

K. Ando, T. Kobayashi, N. Uchida, Org. Lett., 2015, 17, 2554-2557.

DOI: 10.1021/acs.orglett.5b01049 (free Supporting Information)


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Abstract

1-methyl-2-(methylsulfonyl)benzimidazole reacts with a variety of aldehydes and ketones in the presence of either NaHMDS (-55 C to rt) or t-BuOK (rt, 1 h) in DMF to give the corresponding terminal alkenes in high yields. The byproducts of this Julia-type methylenation reagent are easily removed, and the reaction conditions are mild and practical.

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proposed mechanism



Key Words

Julia-Kocienski Olefination, Terminal Alkenes


ID: J54-Y2015