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Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis
We report a novel and general method to access a highly under‐studied privileged scaffold—pyrimidines bearing a trifluoroborate at C4, and highlight the broad utility of these intermediates in a rich array of downstream functionalization reactions. This chemistry is underpinned by the unique feature...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252621/ https://www.ncbi.nlm.nih.gov/pubmed/33570831 http://dx.doi.org/10.1002/anie.202101297 |
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author | Cousins, David L. Fricero, Prisca Kopf, Kenji P. M. McColl, Elliot J. Czechtizky, Werngard Lim, Yee Hwee Harrity, Joseph P. A. |
author_facet | Cousins, David L. Fricero, Prisca Kopf, Kenji P. M. McColl, Elliot J. Czechtizky, Werngard Lim, Yee Hwee Harrity, Joseph P. A. |
author_sort | Cousins, David L. |
collection | PubMed |
description | We report a novel and general method to access a highly under‐studied privileged scaffold—pyrimidines bearing a trifluoroborate at C4, and highlight the broad utility of these intermediates in a rich array of downstream functionalization reactions. This chemistry is underpinned by the unique features of the trifluoroborate group; its robustness provides an opportunity to carry out chemoselective reactions at other positions on the pyrimidine while providing a pathway for elaboration at the C−B bond when suitably activated. |
format | Online Article Text |
id | pubmed-8252621 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-82526212021-07-09 Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis Cousins, David L. Fricero, Prisca Kopf, Kenji P. M. McColl, Elliot J. Czechtizky, Werngard Lim, Yee Hwee Harrity, Joseph P. A. Angew Chem Int Ed Engl Communications We report a novel and general method to access a highly under‐studied privileged scaffold—pyrimidines bearing a trifluoroborate at C4, and highlight the broad utility of these intermediates in a rich array of downstream functionalization reactions. This chemistry is underpinned by the unique features of the trifluoroborate group; its robustness provides an opportunity to carry out chemoselective reactions at other positions on the pyrimidine while providing a pathway for elaboration at the C−B bond when suitably activated. John Wiley and Sons Inc. 2021-03-17 2021-04-19 /pmc/articles/PMC8252621/ /pubmed/33570831 http://dx.doi.org/10.1002/anie.202101297 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Cousins, David L. Fricero, Prisca Kopf, Kenji P. M. McColl, Elliot J. Czechtizky, Werngard Lim, Yee Hwee Harrity, Joseph P. A. Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis |
title | Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis |
title_full | Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis |
title_fullStr | Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis |
title_full_unstemmed | Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis |
title_short | Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis |
title_sort | pyrimidin‐6‐yl trifluoroborate salts as versatile templates for heterocycle synthesis |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252621/ https://www.ncbi.nlm.nih.gov/pubmed/33570831 http://dx.doi.org/10.1002/anie.202101297 |
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