期刊
ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 11, 期 2, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100700
关键词
tandem reaction; trifluoromethyl group; cyclopentylmagnesium bromide; reduction; deprotonation
We have developed a functional-group-tolerant one-pot method for synthesizing various 3-substituted 1-trifluoromethylpropargyl alcohols. This method involves three successive reactions and can be applied to different fluorine-containing esters and terminal alkynes. The obtained products can be further transformed into important compounds for the treatment of pain and inflammation associated with osteoarthritis in dogs.
We have developed a functional-group-tolerant one-pot route to various 3-substituted 1-trifluoromethylpropargyl alcohols utilizing two reactions of cyclopentylmagnesium bromide with trifluoroacetic acid esters and terminal alkynes. This new synthetic method involves three successive reactions in a one-pot process: 1) deprotonation of terminal alkynes with cyclopentylmagnesium bromide, 2) reduction of 2,2,2-trifluoroethyl trifluoroacetate with cyclopentylmagnesium bromide, and 3) nucleophilic addition of in-situ-generated alkynyl Grignard reagents to in-situ-formed trifluoroacetaldehyde, leading to the corresponding 3-substituted 1-trifluoromethylated propargyl alcohols. This method can be applied to various fluorine-containing esters as well as terminal alkynes bearing alkyl and aryl groups to give 1-polyfluoroalkylated propargyl alcohols. The obtained 1-trifluoromethylpropargyl alcohols with aromatic groups can be converted in good to excellent yields to 1,5-diaryl-3-trifluoromethyl-dihydropyrazoles, some of the most important motifs in medicine for the treatment of pain and inflammation associated with osteoarthritis in dogs.
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