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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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2019
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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. |
format | Online Article Text |
id | pubmed-6778098 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
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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