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Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond
Over the past few decades, photocatalytic C–H functionalization reactions have received increasing attention due to the often mild reaction conditions and complementary selectivities to conventional functionalization processes. Now, photocatalytic C–H functionalization is a widely employed tool, sup...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10664588/ https://www.ncbi.nlm.nih.gov/pubmed/38023504 http://dx.doi.org/10.1039/d3sc04027e |
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author | Yuan, Zheliang Britton, Robert |
author_facet | Yuan, Zheliang Britton, Robert |
author_sort | Yuan, Zheliang |
collection | PubMed |
description | Over the past few decades, photocatalytic C–H functionalization reactions have received increasing attention due to the often mild reaction conditions and complementary selectivities to conventional functionalization processes. Now, photocatalytic C–H functionalization is a widely employed tool, supporting activities ranging from complex molecule synthesis to late-stage structure–activity relationship studies. In this perspective, we will discuss our efforts in developing a photocatalytic decatungstate catalyzed C–H fluorination reaction as well as its practical application realized through collaborations with industry partners at Hoffmann–La Roche and Merck, and extension to radiofluorination with radiopharmaceutical chemists and imaging experts at TRIUMF and the BC Cancer Agency. Importantly, we feel that our efforts address a question of utility posed by Professor Tobias Ritter in “Late-Stage Fluorination: Fancy Novelty or Useful Tool?” (ACIE, 2015, 54, 3216). In addition, we will discuss decatungstate catalyzed C–H fluoroalkylation and the interesting electrostatic effects observed in decatungstate-catalyzed C–H functionalization. We hope this perspective will inspire other researchers to explore the use of decatungstate for the purposes of photocatalytic C–H functionalization and further advance the exploitation of electrostatic effects for both rate acceleration and directing effects in these reactions. |
format | Online Article Text |
id | pubmed-10664588 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-106645882023-11-01 Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond Yuan, Zheliang Britton, Robert Chem Sci Chemistry Over the past few decades, photocatalytic C–H functionalization reactions have received increasing attention due to the often mild reaction conditions and complementary selectivities to conventional functionalization processes. Now, photocatalytic C–H functionalization is a widely employed tool, supporting activities ranging from complex molecule synthesis to late-stage structure–activity relationship studies. In this perspective, we will discuss our efforts in developing a photocatalytic decatungstate catalyzed C–H fluorination reaction as well as its practical application realized through collaborations with industry partners at Hoffmann–La Roche and Merck, and extension to radiofluorination with radiopharmaceutical chemists and imaging experts at TRIUMF and the BC Cancer Agency. Importantly, we feel that our efforts address a question of utility posed by Professor Tobias Ritter in “Late-Stage Fluorination: Fancy Novelty or Useful Tool?” (ACIE, 2015, 54, 3216). In addition, we will discuss decatungstate catalyzed C–H fluoroalkylation and the interesting electrostatic effects observed in decatungstate-catalyzed C–H functionalization. We hope this perspective will inspire other researchers to explore the use of decatungstate for the purposes of photocatalytic C–H functionalization and further advance the exploitation of electrostatic effects for both rate acceleration and directing effects in these reactions. The Royal Society of Chemistry 2023-11-01 /pmc/articles/PMC10664588/ /pubmed/38023504 http://dx.doi.org/10.1039/d3sc04027e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Yuan, Zheliang Britton, Robert Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond |
title | Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond |
title_full | Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond |
title_fullStr | Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond |
title_full_unstemmed | Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond |
title_short | Development and application of decatungstate catalyzed C–H (18)F- and (19)F-fluorination, fluoroalkylation and beyond |
title_sort | development and application of decatungstate catalyzed c–h (18)f- and (19)f-fluorination, fluoroalkylation and beyond |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10664588/ https://www.ncbi.nlm.nih.gov/pubmed/38023504 http://dx.doi.org/10.1039/d3sc04027e |
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