Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

Regioselective amino-difluoromethylation of aromatic alkenes via C(sp(3))–CF(2)H and C(sp(3))–N bond formation with the C[double bond, length as m-dash]C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfoni...

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Detalles Bibliográficos
Autores principales: Noto, Naoki, Koike, Takashi, Akita, Munetaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5628600/
https://www.ncbi.nlm.nih.gov/pubmed/28989669
http://dx.doi.org/10.1039/c7sc01703k
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author Noto, Naoki
Koike, Takashi
Akita, Munetaka
author_facet Noto, Naoki
Koike, Takashi
Akita, Munetaka
author_sort Noto, Naoki
collection PubMed
description Regioselective amino-difluoromethylation of aromatic alkenes via C(sp(3))–CF(2)H and C(sp(3))–N bond formation with the C[double bond, length as m-dash]C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, S-difluoromethyl-S-di(p-xylyl)sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermore, this noble metal-free protocol allows for the photocatalytic trifluoromethylation of alkenes.
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spelling pubmed-56286002017-10-06 Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis Noto, Naoki Koike, Takashi Akita, Munetaka Chem Sci Chemistry Regioselective amino-difluoromethylation of aromatic alkenes via C(sp(3))–CF(2)H and C(sp(3))–N bond formation with the C[double bond, length as m-dash]C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, S-difluoromethyl-S-di(p-xylyl)sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermore, this noble metal-free protocol allows for the photocatalytic trifluoromethylation of alkenes. Royal Society of Chemistry 2017-09-01 2017-07-10 /pmc/articles/PMC5628600/ /pubmed/28989669 http://dx.doi.org/10.1039/c7sc01703k Text en This journal is © The Royal Society of Chemistry 2017 https://creativecommons.org/licenses/by-nc/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/ (https://creativecommons.org/licenses/by-nc/3.0/) ) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Noto, Naoki
Koike, Takashi
Akita, Munetaka
Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
title Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
title_full Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
title_fullStr Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
title_full_unstemmed Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
title_short Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
title_sort metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5628600/
https://www.ncbi.nlm.nih.gov/pubmed/28989669
http://dx.doi.org/10.1039/c7sc01703k
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