Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne

The regioselective carbon–carbon bond formation was studied using 5,5,5-trifluoro-1-phenylpent-3-en-1-yne as a model substrate, and predominant acceptance of electrophiles β to a CF(3) group as well as a deuterium trap experiment of the lithiated species led to the conclusion that the obtained regio...

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Detalles Bibliográficos
Autores principales: Naka, Motoki, Kawasaki-Takasuka, Tomoko, Yamazaki, Takashi
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/PMC3817480/
https://www.ncbi.nlm.nih.gov/pubmed/24204431
http://dx.doi.org/10.3762/bjoc.9.256
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author Naka, Motoki
Kawasaki-Takasuka, Tomoko
Yamazaki, Takashi
author_facet Naka, Motoki
Kawasaki-Takasuka, Tomoko
Yamazaki, Takashi
author_sort Naka, Motoki
collection PubMed
description The regioselective carbon–carbon bond formation was studied using 5,5,5-trifluoro-1-phenylpent-3-en-1-yne as a model substrate, and predominant acceptance of electrophiles β to a CF(3) group as well as a deuterium trap experiment of the lithiated species led to the conclusion that the obtained regioselectivity is kinetically determined for the reactions with electrophiles, under equilibration of the possible two anionic species.
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spelling pubmed-38174802013-11-07 Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne Naka, Motoki Kawasaki-Takasuka, Tomoko Yamazaki, Takashi Beilstein J Org Chem Full Research Paper The regioselective carbon–carbon bond formation was studied using 5,5,5-trifluoro-1-phenylpent-3-en-1-yne as a model substrate, and predominant acceptance of electrophiles β to a CF(3) group as well as a deuterium trap experiment of the lithiated species led to the conclusion that the obtained regioselectivity is kinetically determined for the reactions with electrophiles, under equilibration of the possible two anionic species. Beilstein-Institut 2013-10-23 /pmc/articles/PMC3817480/ /pubmed/24204431 http://dx.doi.org/10.3762/bjoc.9.256 Text en Copyright © 2013, Naka 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
Naka, Motoki
Kawasaki-Takasuka, Tomoko
Yamazaki, Takashi
Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
title Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
title_full Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
title_fullStr Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
title_full_unstemmed Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
title_short Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
title_sort regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817480/
https://www.ncbi.nlm.nih.gov/pubmed/24204431
http://dx.doi.org/10.3762/bjoc.9.256
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