Visible-light-driven selective difluoroalkylation of α-CF3 alkenes to access CF2-containing gem-difluoroalkenes and trifluoromethylalkanes

文献情報

出版日 2023-11-23

DOI 10.1039/D3QO01551C

インパクトファクター 5.281

著者

Panpan Lei, Bingran Chen, Tonghui Zhang, Qinlin Chen, Liangming Xuan, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jie Zeng

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要旨

An efficient visible-light-promoted selective difluoroalkylation of α-trifluoromethyl alkenes with difluoroalkylating reagents has been achieved via intermolecular difluoroalkyl radical addition mediated by photoredox catalysis under metal-free conditions. This transformation proceeded smoothly in the presence of the organic dye 4CzIPN, affording a series of gem-difluoroalkene difluoroacetates and trifluoromethylated difluoroacetamides in moderate to excellent yields. The chemoselectivity of the process (β-F elimination or protonation) is controlled by adjusting the bromodifluoro substrates. This protocol is distinguished by its mild conditions, wide scope, and exquisite chemoselectivity. Moreover, theoretical calculations revealed the important role of the N–H bond of bromodifluoroacetates in the control of the selectivity.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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