Four-component acyloxy-trifluoromethylation of arylalkenes mediated by a photoredox catalyst

A four-component intermolecular trifluoromethylation-acyloxylation of arylalkenes induced by visible light has been developed in the presence of the photoredox catalyst Ru(bpy)3(PF6)2 under mild reaction conditions. A new Umemoto's reagent was used as a trifluoromethyl radical source, and this...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019, Vol.17 (1), p.24-29
Main Authors: Zhou, Xiaocong, Li, Guijie, Shao, Zongzhou, Fang, Kun, Gao, Hongjun, Li, Yuanqiang, She, Yuanbin
Format: Article
Language:English
Subjects:
Alkenes
Aromatic compounds
Catalysis
Catalysts
Chemical compounds
Deuterium
Dimethylformamide
Functional groups
NMR
Nuclear magnetic resonance
Organic chemistry
Reagents
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Summary:A four-component intermolecular trifluoromethylation-acyloxylation of arylalkenes induced by visible light has been developed in the presence of the photoredox catalyst Ru(bpy)3(PF6)2 under mild reaction conditions. A new Umemoto's reagent was used as a trifluoromethyl radical source, and this redox neutral reaction demonstrated good functional group tolerance for aryl alkenes with high yields up to 91%. The detailed reaction process was investigated based on control, deuterium and O18-labeling experiments to support that N,N-dimethylformamide (DMF)/H2O acted as an acyloxyl source.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02239a