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Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-cat...

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Autores principales: Nambo, Masakazu, Yim, Jacky C.-H., Freitas, Luiza B. O., Tahara, Yasuyo, Ariki, Zachary T., Maekawa, Yuuki, Yokogawa, Daisuke, Crudden, Cathleen M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6778098/
https://www.ncbi.nlm.nih.gov/pubmed/31586048
http://dx.doi.org/10.1038/s41467-019-11758-w
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author Nambo, Masakazu
Yim, Jacky C.-H.
Freitas, Luiza B. O.
Tahara, Yasuyo
Ariki, Zachary T.
Maekawa, Yuuki
Yokogawa, Daisuke
Crudden, Cathleen M.
author_facet Nambo, Masakazu
Yim, Jacky C.-H.
Freitas, Luiza B. O.
Tahara, Yasuyo
Ariki, Zachary T.
Maekawa, Yuuki
Yokogawa, Daisuke
Crudden, Cathleen M.
author_sort Nambo, Masakazu
collection PubMed
description α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.
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spelling pubmed-67780982019-10-07 Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling Nambo, Masakazu Yim, Jacky C.-H. Freitas, Luiza B. O. Tahara, Yasuyo Ariki, Zachary T. Maekawa, Yuuki Yokogawa, Daisuke Crudden, Cathleen M. Nat Commun Article α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs. Nature Publishing Group UK 2019-10-04 /pmc/articles/PMC6778098/ /pubmed/31586048 http://dx.doi.org/10.1038/s41467-019-11758-w Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Nambo, Masakazu
Yim, Jacky C.-H.
Freitas, Luiza B. O.
Tahara, Yasuyo
Ariki, Zachary T.
Maekawa, Yuuki
Yokogawa, Daisuke
Crudden, Cathleen M.
Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
title Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
title_full Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
title_fullStr Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
title_full_unstemmed Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
title_short Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
title_sort modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6778098/
https://www.ncbi.nlm.nih.gov/pubmed/31586048
http://dx.doi.org/10.1038/s41467-019-11758-w
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