Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations

Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C–C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fl...

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Autores principales: Pitts, Cody Ross, Bloom, Michelle Sheanne, Bume, Desta Doro, Zhang, Qinze Arthur, Lectka, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5669245/
https://www.ncbi.nlm.nih.gov/pubmed/29449927
http://dx.doi.org/10.1039/c5sc01973g
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author Pitts, Cody Ross
Bloom, Michelle Sheanne
Bume, Desta Doro
Zhang, Qinze Arthur
Lectka, Thomas
author_facet Pitts, Cody Ross
Bloom, Michelle Sheanne
Bume, Desta Doro
Zhang, Qinze Arthur
Lectka, Thomas
author_sort Pitts, Cody Ross
collection PubMed
description Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C–C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fluoro carboxylic acids, esters, alcohols, and ketones with relative ease. Initial mechanistic insight suggests radical ion intermediates.
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spelling pubmed-56692452018-02-15 Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations Pitts, Cody Ross Bloom, Michelle Sheanne Bume, Desta Doro Zhang, Qinze Arthur Lectka, Thomas Chem Sci Chemistry Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C–C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fluoro carboxylic acids, esters, alcohols, and ketones with relative ease. Initial mechanistic insight suggests radical ion intermediates. Royal Society of Chemistry 2015-09-01 2015-06-23 /pmc/articles/PMC5669245/ /pubmed/29449927 http://dx.doi.org/10.1039/c5sc01973g Text en This journal is © The Royal Society of Chemistry 2015 http://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/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Pitts, Cody Ross
Bloom, Michelle Sheanne
Bume, Desta Doro
Zhang, Qinze Arthur
Lectka, Thomas
Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations
title Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations
title_full Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations
title_fullStr Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations
title_full_unstemmed Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations
title_short Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations
title_sort unstrained c–c bond activation and directed fluorination through photocatalytically-generated radical cations
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5669245/
https://www.ncbi.nlm.nih.gov/pubmed/29449927
http://dx.doi.org/10.1039/c5sc01973g
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