Nickel-catalyzed defluorinative alkylation of C(sp2)–F bonds

文献信息

发布日期 2021-06-07

DOI 10.1039/D1QO00549A

影响因子 5.281

作者

Xue Tong, Si-Si Luo, Hua Shen, Shu Zhang, Tian Cao, Yi-Peng Luo, Long-Ling Huang, Xi-Tao Ma, Xiang-Wei Liu

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摘要

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.

期刊推荐

Drug and Chemical Toxicology

Studies in Conservation

Dental Materials

Synthetic Communications

Progress in Materials Science

Applied Clay Science

Dyes and Pigments

Annual Review of Public Health

Organic Geochemistry

Applied Surface Science

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 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

Nickel-catalyzed defluorinative alkylation of C(sp2)–F bonds

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