Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes

[Image: see text] This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp(2))–H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in...

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Autores principales: McCammant, Matthew S., Thompson, Stephen, Brooks, Allen F., Krska, Shane W., Scott, Peter J. H., Sanford, Melanie S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5525103/
https://www.ncbi.nlm.nih.gov/pubmed/28665619
http://dx.doi.org/10.1021/acs.orglett.7b01902
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author McCammant, Matthew S.
Thompson, Stephen
Brooks, Allen F.
Krska, Shane W.
Scott, Peter J. H.
Sanford, Melanie S.
author_facet McCammant, Matthew S.
Thompson, Stephen
Brooks, Allen F.
Krska, Shane W.
Scott, Peter J. H.
Sanford, Melanie S.
author_sort McCammant, Matthew S.
collection PubMed
description [Image: see text] This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp(2))–H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in a Cu-mediated radiofluorination with [(18)F]KF. This approach leverages the stability and availability of electron-rich arene starting materials to enable mild late-stage radiofluorination of toluene, anisole, aniline, pyrrole, and thiophene derivatives. The radiofluorination has been automated to access a 41 mCi dose of an (18)F-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity.
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spelling pubmed-55251032017-08-03 Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes McCammant, Matthew S. Thompson, Stephen Brooks, Allen F. Krska, Shane W. Scott, Peter J. H. Sanford, Melanie S. Org Lett [Image: see text] This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp(2))–H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in a Cu-mediated radiofluorination with [(18)F]KF. This approach leverages the stability and availability of electron-rich arene starting materials to enable mild late-stage radiofluorination of toluene, anisole, aniline, pyrrole, and thiophene derivatives. The radiofluorination has been automated to access a 41 mCi dose of an (18)F-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity. American Chemical Society 2017-06-30 2017-07-21 /pmc/articles/PMC5525103/ /pubmed/28665619 http://dx.doi.org/10.1021/acs.orglett.7b01902 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle McCammant, Matthew S.
Thompson, Stephen
Brooks, Allen F.
Krska, Shane W.
Scott, Peter J. H.
Sanford, Melanie S.
Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes
title Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes
title_full Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes
title_fullStr Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes
title_full_unstemmed Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes
title_short Cu-Mediated C–H (18)F-Fluorination of Electron-Rich (Hetero)arenes
title_sort cu-mediated c–h (18)f-fluorination of electron-rich (hetero)arenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5525103/
https://www.ncbi.nlm.nih.gov/pubmed/28665619
http://dx.doi.org/10.1021/acs.orglett.7b01902
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