Oxidative 3,3,3-trifluoropropylation of arylaldehydes

A reaction between (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane (1) and arylaldehydes 2 was triggered by fluoride anions to afford aryl 3,3,3-trifluoropropyl ketones 3 in moderate to good yield. A mechanistic study of this reaction indicated that it occurred via an allyl alkoxide (4). A subseq...

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Published inBeilstein journal of organic chemistry Vol. 9; no. 1; pp. 2417 - 2421
Main Authors Ikeda, Akari, Omote, Masaaki, Nomura, Shiho, Tanaka, Miyuu, Tarui, Atsushi, Sato, Kazuyuki, Ando, Akira
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 11.11.2013
Subjects
1,3-proton shift
3,3,3-trifluoropropenyl
cesium fluoride
Chemistry
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organo-fluorine
trifluoromethyl
trifluoromethyl
3,3,3-trifluoropropenyl
cesium fluoride
1,3-proton shift
organo-fluorine
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Summary:A reaction between (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane (1) and arylaldehydes 2 was triggered by fluoride anions to afford aryl 3,3,3-trifluoropropyl ketones 3 in moderate to good yield. A mechanistic study of this reaction indicated that it occurred via an allyl alkoxide (4). A subsequent 1,3-proton shift of the benzylic proton of 4 forms 3. This reaction involves oxidative 3,3,3-trifluoropropylation of an arylaldehyde to afford 4,4,4-trifluoro-1-arylbutan-1-one.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.9.279