Nickel-catalyzed defluorinative alkylation of C(sp2)–F bonds
Literature Information
Publication Date
2021-06-07
DOI
10.1039/D1QO00549A
Impact Factor
5.281
Authors
Xue Tong, Si-Si Luo, Hua Shen, Shu Zhang, Tian Cao, Yi-Peng Luo, Long-Ling Huang, Xi-Tao Ma, Xiang-Wei Liu
View Original
Abstract
The direct conversion of a C(sp2)–F bond into the corresponding C(sp2)–C(sp3) bond using Al(alkyl)3 as the coupling partner under nickel catalysis is reported. Intriguingly, aryl fluorides, alkenyl monofluorides, and alkenyl gem-difluorides are viable electrophiles in this transformation, constituting the notable feature of this protocol. The success of this chemoselective method relies on the fluorophilicity of the employed aluminum reagent that functions as both the Lewis acid for the activation of the challenging C–F bond and the corresponding alkylating partner. Successful application of this strategy to the late-stage C–F alkylation of fluorinated drug analogue is also demonstrated. This method represents another important example of using challenging C–F bonds as alternative electrophiles.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
CAS Number:
1020174-04-2
Molecular Formula:
C10H17BN2O2
![4-{2-[4-(2-Methyl-2-propanyl)phenyl]ethoxy}quinazoline structure](https://static.chemtradehub.com/structs/120/120928-09-8-d3db.webp "4-{2-[4-(2-Methyl-2-propanyl)phenyl]ethoxy}quinazoline structure")
4-{2-[4-(2-Methyl-2-propanyl)phenyl]ethoxy}quinazoline
CAS Number:
120928-09-8
Molecular Formula:
C20H22N2O
(1H-Benzotriazol-1-yloxy)(di-1-pyrrolidinyl)methylium hexafluorophosphate
CAS Number:
105379-24-6
Molecular Formula:
C15H21F6N5OP
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