Ketones as directing groups in photocatalytic sp(3) C–H fluorination

The ubiquitous ketone carbonyl group generally deactivates substrates toward radical-based fluorinations, especially sites closest to it. Herein, ketones are used instead to direct aliphatic fluorination using Selectfluor, catalytic benzil, and visible light. Selective β- and γ-fluorination are demo...

Descripción completa

Detalles Bibliográficos
Autores principales: Bume, Desta Doro, Pitts, Cody Ross, Ghorbani, Fereshte, Harry, Stefan Andrew, Capilato, Joseph N., Siegler, Maxime A., Lectka, Thomas
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/PMC5637129/
https://www.ncbi.nlm.nih.gov/pubmed/29147517
http://dx.doi.org/10.1039/c7sc02703f
_version_ 1783270574207795200
author Bume, Desta Doro
Pitts, Cody Ross
Ghorbani, Fereshte
Harry, Stefan Andrew
Capilato, Joseph N.
Siegler, Maxime A.
Lectka, Thomas
author_facet Bume, Desta Doro
Pitts, Cody Ross
Ghorbani, Fereshte
Harry, Stefan Andrew
Capilato, Joseph N.
Siegler, Maxime A.
Lectka, Thomas
author_sort Bume, Desta Doro
collection PubMed
description The ubiquitous ketone carbonyl group generally deactivates substrates toward radical-based fluorinations, especially sites closest to it. Herein, ketones are used instead to direct aliphatic fluorination using Selectfluor, catalytic benzil, and visible light. Selective β- and γ-fluorination are demonstrated on rigid mono-, di-, tri-, and tetracyclic (steroidal) substrates employing both cyclic and exocyclic aliphatic ketones as directing groups.
format Online
Article
Text
id pubmed-5637129
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-56371292017-11-16 Ketones as directing groups in photocatalytic sp(3) C–H fluorination Bume, Desta Doro Pitts, Cody Ross Ghorbani, Fereshte Harry, Stefan Andrew Capilato, Joseph N. Siegler, Maxime A. Lectka, Thomas Chem Sci Chemistry The ubiquitous ketone carbonyl group generally deactivates substrates toward radical-based fluorinations, especially sites closest to it. Herein, ketones are used instead to direct aliphatic fluorination using Selectfluor, catalytic benzil, and visible light. Selective β- and γ-fluorination are demonstrated on rigid mono-, di-, tri-, and tetracyclic (steroidal) substrates employing both cyclic and exocyclic aliphatic ketones as directing groups. Royal Society of Chemistry 2017-10-01 2017-08-11 /pmc/articles/PMC5637129/ /pubmed/29147517 http://dx.doi.org/10.1039/c7sc02703f Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Bume, Desta Doro
Pitts, Cody Ross
Ghorbani, Fereshte
Harry, Stefan Andrew
Capilato, Joseph N.
Siegler, Maxime A.
Lectka, Thomas
Ketones as directing groups in photocatalytic sp(3) C–H fluorination
title Ketones as directing groups in photocatalytic sp(3) C–H fluorination
title_full Ketones as directing groups in photocatalytic sp(3) C–H fluorination
title_fullStr Ketones as directing groups in photocatalytic sp(3) C–H fluorination
title_full_unstemmed Ketones as directing groups in photocatalytic sp(3) C–H fluorination
title_short Ketones as directing groups in photocatalytic sp(3) C–H fluorination
title_sort ketones as directing groups in photocatalytic sp(3) c–h fluorination
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5637129/
https://www.ncbi.nlm.nih.gov/pubmed/29147517
http://dx.doi.org/10.1039/c7sc02703f
work_keys_str_mv AT bumedestadoro ketonesasdirectinggroupsinphotocatalyticsp3chfluorination
AT pittscodyross ketonesasdirectinggroupsinphotocatalyticsp3chfluorination
AT ghorbanifereshte ketonesasdirectinggroupsinphotocatalyticsp3chfluorination
AT harrystefanandrew ketonesasdirectinggroupsinphotocatalyticsp3chfluorination
AT capilatojosephn ketonesasdirectinggroupsinphotocatalyticsp3chfluorination
AT sieglermaximea ketonesasdirectinggroupsinphotocatalyticsp3chfluorination
AT lectkathomas ketonesasdirectinggroupsinphotocatalyticsp3chfluorination

Ejemplares similares