Visible-light-driven selective difluoroalkylation of α-CF3 alkenes to access CF2-containing gem-difluoroalkenes and trifluoromethylalkanes
Literature Information
Publication Date
2023-11-23
DOI
10.1039/D3QO01551C
Impact Factor
5.281
Authors
Panpan Lei, Bingran Chen, Tonghui Zhang, Qinlin Chen, Liangming Xuan, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jie Zeng
View Original
Abstract
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.
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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
2-Methyl-2-propanyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate
CAS Number:
211429-79-7
Molecular Formula:
C15H17NO3
![N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide structure](https://static.chemtradehub.com/structs/142/1426944-49-1-1e4c.webp "N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide structure")
N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide
CAS Number:
1426944-49-1
Molecular Formula:
C25H28ClN3O
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