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- Title
Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent.
- Authors
Liang, Yufan; Fu, Gregory C.
- Abstract
Fluorinated organic molecules are of interest in fields ranging from medicinal chemistry to polymer science. Described herein is a mild, convenient, and versatile method for the synthesis of compounds bearing a perfluoroalkyl group attached to a tertiary carbon atom by using an alkyl-alkyl cross-coupling. A nickel catalyst derived from 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 is 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 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) inhibits cross-coupling under these conditions and that a TEMPO-electrophile adduct can be isolated.
- Subjects
ELECTROPHILES; FLUORINATION; NICKEL catalysts; COUPLING reactions (Chemistry); SUBSTITUENTS (Chemistry); FUNCTIONAL groups
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 31, p9175
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201503297