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Nickel-Catalyzed Alkyl–Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent
- Publication Year :
- 2015
- Publisher :
- Wiley, 2015.
-
Abstract
- Fluorinated organic molecules are of interest in fields ranging from medicinal chemistry to polymer science. Herein, we describe a mild, convenient, and versatile method for the synthesis of compounds that bear a perfluoroalkyl group attached to a tertiary carbon, via an alkyl–alkyl cross-coupling. Thus, a nickel catalyst derived from commercially available components (NiCl2·glyme and a pybox ligand) achieves the coupling of a wide range of fluorinated alkyl halides with alkylzinc reagents at room temperature. A broad array of functional groups (e.g., alkyne, aryl iodide, carbamate, furan, ketone, nitrile, phosphonate, primary alkyl bromide, and primary alkyl tosylate) are compatible with the reaction conditions, and highly selective couplings can be achieved on the basis of differing levels of fluorination. A mechanistic investigation has established that the presence of TEMPO inhibits cross-coupling under these conditions and that a TEMPO–electrophile adduct can be isolated.
- Subjects :
- chemistry.chemical_classification
Halogenation
Molecular Structure
Substituent
chemistry.chemical_element
Homogeneous catalysis
Stereoisomerism
General Chemistry
General Medicine
Article
Catalysis
Adduct
chemistry.chemical_compound
Zinc
chemistry
Nickel
Electrophile
Polymer chemistry
Fluorine
Organic chemistry
Alkyl
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....b516a762403495c11f9d59cec1ba747a