Journal
ALDRICHIMICA ACTA
Volume 55, Issue 1, Pages 17-24Publisher
ALDRICH CHEMICAL CO INC
Keywords
perfluoroalkylation; trifluoromethylation; radical reaction; difunctionalization of alkenes; intramolecular cyclization; Togni reagent; perfluorocarboxylic anhydride; copper catalyst; carbocycle; heterocycle
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Funding
- JSPS KAKENHI [21K06489]
- Grants-in-Aid for Scientific Research [21K06489] Funding Source: KAKEN
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Fluoroalkylation is an important strategy for enhancing the drug-like properties and bioactivities of compounds. This mini-review focuses on intramolecular difunctionalization-type fluoroalkylations of alkenes using Togni reagent and fluorine-containing carboxylic anhydrides. These reactions yield fluoroalkyl-group-containing carbo- and heterocycles as potential bioactive compounds.
Fluoroalkylation is often an effective strategy for improving the drug-like properties and bioactivities of compounds such as pharmaceuticals and agrochemicals. Efficient and practical fluoroalkylation methods are therefore important tools in the synthetic chemist's tool chest. In particular, difunctionalization-type fluoroalkylations of alkenes-installing a fluoroalkyl group and constructing a cyclic skeleton simultaneously-pose a significant challenge for synthetic organic chemists. Focusing mainly on work in our laboratory, this mini-review summarizes intramolecular difunctionalization-type fluoroalkylations of alkenes with Togni reagent and fluorine-containing carboxylic anhydrides. These reactions lead to a variety of fluoroalkyl-group-containing carbo- and heterocycles as potentially bioactive molecules and building blocks suitable for further elaboration.
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