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

A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)­benzimidazole (1e), 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 are easily remov...

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Bibliographic Details
Published in:Organic letters 2015-05, Vol.17 (10), p.2554-2557
Main Authors: Ando, Kaori, Kobayashi, Takahisa, Uchida, Nariaki
Format: Article
Language:English
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Summary:A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)­benzimidazole (1e), 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 are easily removed, and the reaction conditions are mild and practical.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01049