title: Oxidative 3,3,3-trifluoropropylation of arylaldehydes.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Akari
authors.initials: A
authors.lastname: Ikeda
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Masaaki
authors.initials: M
authors.lastname: Omote
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Shiho
authors.initials: S
authors.lastname: Nomura
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Miyuu
authors.initials: M
authors.lastname: Tanaka
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Tarui
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Sato
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Ando
keywords: 1,3-proton shift; 3,3,3-trifluoropropenyl; cesium fluoride; organo-fluorine; trifluoromethyl