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Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates

[Image: see text] Polyfluorinated biphenyls are interesting and promising substrates for many different applications. Unfortunately, all current methods for the syntheses of these compounds only work for a hand full of molecules or only in very special cases. Thus, many of these compounds are still...

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Autores principales: Bulfield, David, Huber, Stefan M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5746848/
https://www.ncbi.nlm.nih.gov/pubmed/29156885
http://dx.doi.org/10.1021/acs.joc.7b02267
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author Bulfield, David
Huber, Stefan M.
author_facet Bulfield, David
Huber, Stefan M.
author_sort Bulfield, David
collection PubMed
description [Image: see text] Polyfluorinated biphenyls are interesting and promising substrates for many different applications. Unfortunately, all current methods for the syntheses of these compounds only work for a hand full of molecules or only in very special cases. Thus, many of these compounds are still inaccessible to date. Here we report a general strategy for the synthesis of a wide range of highly fluorinated biphenyls. In our studies we investigated crucial parameters, such as different phosphine ligands and the influence of various nucleophiles and electrophiles with different degrees of fluorination. These results extend the scope of the already very versatile Suzuki–Miyaura reaction toward the synthesis of very electron-poor products, making these more readily accessible. The presented methodology is scalable and versatile without the need for elaborate phosphine ligands or Pd-precatalysts.
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spelling pubmed-57468482017-12-31 Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates Bulfield, David Huber, Stefan M. J Org Chem [Image: see text] Polyfluorinated biphenyls are interesting and promising substrates for many different applications. Unfortunately, all current methods for the syntheses of these compounds only work for a hand full of molecules or only in very special cases. Thus, many of these compounds are still inaccessible to date. Here we report a general strategy for the synthesis of a wide range of highly fluorinated biphenyls. In our studies we investigated crucial parameters, such as different phosphine ligands and the influence of various nucleophiles and electrophiles with different degrees of fluorination. These results extend the scope of the already very versatile Suzuki–Miyaura reaction toward the synthesis of very electron-poor products, making these more readily accessible. The presented methodology is scalable and versatile without the need for elaborate phosphine ligands or Pd-precatalysts. American Chemical Society 2017-11-21 2017-12-15 /pmc/articles/PMC5746848/ /pubmed/29156885 http://dx.doi.org/10.1021/acs.joc.7b02267 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 Bulfield, David
Huber, Stefan M.
Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
title Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
title_full Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
title_fullStr Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
title_full_unstemmed Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
title_short Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
title_sort synthesis of polyflourinated biphenyls; pushing the boundaries of suzuki–miyaura cross coupling with electron-poor substrates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5746848/
https://www.ncbi.nlm.nih.gov/pubmed/29156885
http://dx.doi.org/10.1021/acs.joc.7b02267
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