Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone
The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.
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 removed, and the reaction conditions are mild and practical.
Ando, Kaori,Kobayashi, Takahisa,Uchida, Nariaki
supporting information
p. 2554 - 2557
(2015/05/27)
Imidazole compounds and their use as transglutaminase inhibitors
Imidazole compounds including imidazoles and imidazolium salts, and their use as transglutaminase inhibitors are disclosed.
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(2008/06/13)
REDUCTION OF BENZIMIDAZOLE-2-SULFONIC ACIDS
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Popov, I. I.,Boroshko, S. L.,Tertov, B. A.
p. 224
(2007/10/02)
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