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Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins

[Image: see text] Highly substituted coumarins, privileged and versatile scaffolds for bioactive natural products and fluorescence imaging, are obtained via a Pd(II)-catalyzed direct C–H alkenylation reaction (Fujiwara–Moritani reaction), which has emerged as a powerful tool for the construction and...

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Autores principales: Ortiz-de-Elguea, Verónica, Carral-Menoyo, Asier, Simón-Vidal, Lorena, Martinez-Nunes, Mikel, Barbolla, Iratxe, Lete, Marta G., Sotomayor, Nuria, Lete, Esther
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8581981/
https://www.ncbi.nlm.nih.gov/pubmed/34778620
http://dx.doi.org/10.1021/acsomega.1c03469
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author Ortiz-de-Elguea, Verónica
Carral-Menoyo, Asier
Simón-Vidal, Lorena
Martinez-Nunes, Mikel
Barbolla, Iratxe
Lete, Marta G.
Sotomayor, Nuria
Lete, Esther
author_facet Ortiz-de-Elguea, Verónica
Carral-Menoyo, Asier
Simón-Vidal, Lorena
Martinez-Nunes, Mikel
Barbolla, Iratxe
Lete, Marta G.
Sotomayor, Nuria
Lete, Esther
author_sort Ortiz-de-Elguea, Verónica
collection PubMed
description [Image: see text] Highly substituted coumarins, privileged and versatile scaffolds for bioactive natural products and fluorescence imaging, are obtained via a Pd(II)-catalyzed direct C–H alkenylation reaction (Fujiwara–Moritani reaction), which has emerged as a powerful tool for the construction and functionalization of heterocyclic compounds because of its chemical versatility and its environmental advantages. Thus, a selective 6-endo cyclization led to 4-substituted coumarins in moderate yields. Selected examples have been further functionalized in C3 through a second intermolecular C–H alkenylation reaction to give coumarin-acrylate hybrids, whose fluorescence spectra have been measured.
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spelling pubmed-85819812021-11-12 Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins Ortiz-de-Elguea, Verónica Carral-Menoyo, Asier Simón-Vidal, Lorena Martinez-Nunes, Mikel Barbolla, Iratxe Lete, Marta G. Sotomayor, Nuria Lete, Esther ACS Omega [Image: see text] Highly substituted coumarins, privileged and versatile scaffolds for bioactive natural products and fluorescence imaging, are obtained via a Pd(II)-catalyzed direct C–H alkenylation reaction (Fujiwara–Moritani reaction), which has emerged as a powerful tool for the construction and functionalization of heterocyclic compounds because of its chemical versatility and its environmental advantages. Thus, a selective 6-endo cyclization led to 4-substituted coumarins in moderate yields. Selected examples have been further functionalized in C3 through a second intermolecular C–H alkenylation reaction to give coumarin-acrylate hybrids, whose fluorescence spectra have been measured. American Chemical Society 2021-10-25 /pmc/articles/PMC8581981/ /pubmed/34778620 http://dx.doi.org/10.1021/acsomega.1c03469 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Ortiz-de-Elguea, Verónica
Carral-Menoyo, Asier
Simón-Vidal, Lorena
Martinez-Nunes, Mikel
Barbolla, Iratxe
Lete, Marta G.
Sotomayor, Nuria
Lete, Esther
Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
title Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
title_full Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
title_fullStr Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
title_full_unstemmed Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
title_short Pd(II)-Catalyzed Fujiwara–Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
title_sort pd(ii)-catalyzed fujiwara–moritani reactions for the synthesis and functionalization of substituted coumarins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8581981/
https://www.ncbi.nlm.nih.gov/pubmed/34778620
http://dx.doi.org/10.1021/acsomega.1c03469
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