Acylmonofluoromethylation of alkenes via dual NHC/photoredox catalysis
Literature Information
Publication Date
2023-10-24
DOI
10.1039/D3QO01376F
Impact Factor
5.281
Authors
Shichao Tian, Mingxi Chen, Yihan Tang, Keguang Cheng, Gavin Chit Tsui, Quande Wang
View Original
Abstract
Monofluoromethylated compounds exhibit unique physicochemical properties with wide applications in drug discovery. The direct monofluoromethylation of common feedstocks such as alkenes is an attractive approach. Herein, we report a novel three-component radical acylmonofluoromethylation of alkenes by cooperative NHC/photoredox catalysis to synthesize various monofluorinated alkyl aryl ketones. This protocol proceeds through radical–radical coupling of ketyl radicals with benzylic C-radicals. This reaction features broad substrate scope, excellent functional group tolerance and mild conditions. Also, facile late-stage modification of drug molecules and natural products is demonstrated. The SET oxidative generation of monofluoromethyl radicals is advantageous over the use of excess exogenous oxidants, and may open up new avenues for the preparation of monofluorinated building blocks.
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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
Tert-butyl 3-iodo-5-nitro-1H-indazole-1-carboxylate
CAS Number:
459133-69-8
Molecular Formula:
C12H12IN3O4
(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-(tert-butyl)phenyl)butanoic acid
CAS Number:
403661-85-8
Molecular Formula:
C19H29NO4
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