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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...

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Autores principales: Cousins, David L., Fricero, Prisca, Kopf, Kenji P. M., McColl, Elliot J., Czechtizky, Werngard, Lim, Yee Hwee, Harrity, Joseph P. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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.
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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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