Convenient, functional group-tolerant, transition metal-free synthesis of aryl and heteroaryl trifluoromethyl ketones with the use of methyl trifluoroacetate

A new convenient, functional group-tolerant, transition metal-free route to aryl trifluoromethyl ketones under mild conditions is described. The reaction of not only aryl Grignard reagents carrying reducible electrophilic functional groups, such as ester and cyano groups, but also electron-deficient...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (6), p.913-918
Main Authors: Funabiki, Kazumasa, Hayakawa, Ayaka, Inuzuka, Toshiyasu
Format: Article
Language:English
Subjects:
Anticancer properties
Antitumor agents
Aromatic compounds
Cyano groups
Functional groups
Ketones
Metals
Reagents
Trifluoroacetates
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Summary:A new convenient, functional group-tolerant, transition metal-free route to aryl trifluoromethyl ketones under mild conditions is described. The reaction of not only aryl Grignard reagents carrying reducible electrophilic functional groups, such as ester and cyano groups, but also electron-deficient nitrogen-containing heteroaryl Grignard reagents with methyl trifluoroacetate gives the corresponding aryl or heteroaryl trifluoromethyl ketones in good yields. Biological assays revealed that new heteroaryl trifluoromethyl ketones carrying 2,4-dimethoxypyrimidine and 3,5-dimethylisoxazole rings show good anti-tumor activities.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02862h