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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Detalles Bibliográficos
Autores principales: Ikeda, Akari, Omote, Masaaki, Nomura, Shiho, Tanaka, Miyuu, Tarui, Atsushi, Sato, Kazuyuki, Ando, Akira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869248/
https://www.ncbi.nlm.nih.gov/pubmed/24367408
http://dx.doi.org/10.3762/bjoc.9.279
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author Ikeda, Akari
Omote, Masaaki
Nomura, Shiho
Tanaka, Miyuu
Tarui, Atsushi
Sato, Kazuyuki
Ando, Akira
author_facet Ikeda, Akari
Omote, Masaaki
Nomura, Shiho
Tanaka, Miyuu
Tarui, Atsushi
Sato, Kazuyuki
Ando, Akira
author_sort Ikeda, Akari
collection PubMed
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.
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spelling pubmed-38692482013-12-23 Oxidative 3,3,3-trifluoropropylation of arylaldehydes Ikeda, Akari Omote, Masaaki Nomura, Shiho Tanaka, Miyuu Tarui, Atsushi Sato, Kazuyuki Ando, Akira Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-11-11 /pmc/articles/PMC3869248/ /pubmed/24367408 http://dx.doi.org/10.3762/bjoc.9.279 Text en Copyright © 2013, Ikeda et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ikeda, Akari
Omote, Masaaki
Nomura, Shiho
Tanaka, Miyuu
Tarui, Atsushi
Sato, Kazuyuki
Ando, Akira
Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title 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_short Oxidative 3,3,3-trifluoropropylation of arylaldehydes
title_sort oxidative 3,3,3-trifluoropropylation of arylaldehydes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869248/
https://www.ncbi.nlm.nih.gov/pubmed/24367408
http://dx.doi.org/10.3762/bjoc.9.279
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AT taruiatsushi oxidative333trifluoropropylationofarylaldehydes
AT satokazuyuki oxidative333trifluoropropylationofarylaldehydes
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