4.8 Article

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

Journal

ORGANIC LETTERS
Volume 17, Issue 10, Pages 2554-2557

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01049

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Funding

  1. JSPS KAKENHI [25410111]
  2. Grants-in-Aid for Scientific Research [15H00934, 25410111] Funding Source: KAKEN

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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 NaHMLDS (-55 degrees 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.

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