Journal
ORGANIC LETTERS
Volume 17, Issue 19, Pages 4882-4885Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02438
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Funding
- Japan Science and Technology Agency (JST)
- Grants-in-Aid for Scientific Research [26620078] Funding Source: KAKEN
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Difluoromethylation on sp(3) carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the alpha-difluoromethylated nitrile products with an all-carbon quaternary center in moderate to high yields. The Ruppert-Prakash reagent (CF3TMS) is also applicable to the reaction, affording the alpha-siladifluoromethylated nitrile products, which can be utilized for sequential carbon carbon bond-forming reactions. These reactions using 1.1 equiv of lithium base, 1.5-2.0 equiv of CF3H or CF3TMS, and easily accessible nitrile derivatives are completed in only a few minutes, resulting in the formation of valuable difluoromethylated compounds.
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