Practical methylenation reaction for aldehydes and ketones using new Julia-type reagents

Org Lett. 2015 May 15;17(10):2554-7. doi: 10.1021/acs.orglett.5b01049. Epub 2015 May 6.

Abstract

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.