Cargando…
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...
Autores principales: | , , , , , , , |
---|---|
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 |
_version_ | 1784596891552448512 |
---|---|
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. |
format | Online Article Text |
id | pubmed-8581981 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT ortizdeelgueaveronica pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT carralmenoyoasier pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT simonvidallorena pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT martineznunesmikel pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT barbollairatxe pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT letemartag pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT sotomayornuria pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins AT leteesther pdiicatalyzedfujiwaramoritanireactionsforthesynthesisandfunctionalizationofsubstitutedcoumarins |