Organic photoredox catalytic decarboxylative cross-coupling of gem-difluoroalkenes with unactivated carboxylic acids
Literature Information
Publication Date
2019-05-10
DOI
10.1039/C9QO00495E
Impact Factor
5.281
Authors
Hui Yang, Chao Tian, Dongsheng Qiu, Haitao Tian, Guangming Li
View Original
Abstract
The monofluoroalkene substructure plays a crucial role in various fields of organic synthesis, pharmacology and materials science. However, a redox-neutral direct monofluoroalkenylation of prevalent alkyl sources still remains very challenging. Herein, the first monofluoroalkenylation of naturally abundant unactivated carboxylic acids via organic photoredox catalytic decarboxylation has been developed. This redox-neutral approach avoids the utilization of presynthesized redox-active esters and high energy irradiation, providing a mild and efficient strategy for direct decarboxylative cross-coupling reactions of unactivated carboxylic acids. Furthermore, it allows the remarkable and challenging late-stage monofluoroalkenylation of complex molecular architectures such as bioactive ramipril, gemfibrozil, dehydroabietic acid, enoxolone and saccharide-derived cyclic α-oxy acid.
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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-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide structure](https://static.chemtradehub.com/structs/137/1370261-96-3-40df.webp "2-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide structure")
2-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide
CAS Number:
1370261-96-3
Molecular Formula:
C19H23N9O
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