Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 15, Pages 9936-9943Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01227
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Funding
- JSPS KAKENHI [17K05781]
- Grants-in-Aid for Scientific Research [17K05781] Funding Source: KAKEN
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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.
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