Oxidative 3,3,3-trifluoropropylation of arylaldehydes

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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Main Authors: Akari Ikeda, Masaaki Omote, Shiho Nomura, Miyuu Tanaka, Atsushi Tarui, Kazuyuki Sato, Akira Ando
Format: Article
Language:English
Published: Beilstein-Institut 2013-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
cesium fluoride
organo-fluorine
1,3-proton shift
trifluoromethyl
3,3,3-trifluoropropenyl
Online Access:https://doi.org/10.3762/bjoc.9.279
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spelling doaj-34bc8043517145ab8f633f31f093e3222021-02-02T05:48:25ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-11-01912417242110.3762/bjoc.9.2791860-5397-9-279Oxidative 3,3,3-trifluoropropylation of arylaldehydesAkari Ikeda0Masaaki Omote1Shiho Nomura2Miyuu Tanaka3Atsushi Tarui4Kazuyuki Sato5Akira Ando6Faculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45–1, Nagaotoge-cho, Hirakata, Osaka 573–0101, JapanA 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.https://doi.org/10.3762/bjoc.9.279cesium fluorideorgano-fluorine1,3-proton shifttrifluoromethyl3,3,3-trifluoropropenyl
collection DOAJ
language English
format Article
sources DOAJ
author Akari Ikeda
Masaaki Omote
Shiho Nomura
Miyuu Tanaka
Atsushi Tarui
Kazuyuki Sato
Akira Ando
spellingShingle Akari Ikeda
Masaaki Omote
Shiho Nomura
Miyuu Tanaka
Atsushi Tarui
Kazuyuki Sato
Akira Ando
Oxidative 3,3,3-trifluoropropylation of arylaldehydes
Beilstein Journal of Organic Chemistry
cesium fluoride
organo-fluorine
1,3-proton shift
trifluoromethyl
3,3,3-trifluoropropenyl
author_facet Akari Ikeda
Masaaki Omote
Shiho Nomura
Miyuu Tanaka
Atsushi Tarui
Kazuyuki Sato
Akira Ando
author_sort Akari Ikeda
title Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title_short Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title_full Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title_fullStr Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title_full_unstemmed Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title_sort oxidative 3,3,3-trifluoropropylation of arylaldehydes
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2013-11-01
description 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.
topic cesium fluoride
organo-fluorine
1,3-proton shift
trifluoromethyl
3,3,3-trifluoropropenyl
url https://doi.org/10.3762/bjoc.9.279
work_keys_str_mv AT akariikeda oxidative333trifluoropropylationofarylaldehydes
AT masaakiomote oxidative333trifluoropropylationofarylaldehydes
AT shihonomura oxidative333trifluoropropylationofarylaldehydes
AT miyuutanaka oxidative333trifluoropropylationofarylaldehydes
AT atsushitarui oxidative333trifluoropropylationofarylaldehydes
AT kazuyukisato oxidative333trifluoropropylationofarylaldehydes
AT akiraando oxidative333trifluoropropylationofarylaldehydes
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