Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium π-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This...

Descripción completa

Detalles Bibliográficos
Autores principales: Chattopadhyay, Kalicharan, Fenster, Erik, Grenning, Alexander J, Tunge, Jon A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458738/
https://www.ncbi.nlm.nih.gov/pubmed/23019448
http://dx.doi.org/10.3762/bjoc.8.133
_version_ 1782244691426672640
author Chattopadhyay, Kalicharan
Fenster, Erik
Grenning, Alexander J
Tunge, Jon A
author_facet Chattopadhyay, Kalicharan
Fenster, Erik
Grenning, Alexander J
Tunge, Jon A
author_sort Chattopadhyay, Kalicharan
collection PubMed
description The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium π-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.
format Online
Article
Text
id pubmed-3458738
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-34587382012-09-27 Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles Chattopadhyay, Kalicharan Fenster, Erik Grenning, Alexander J Tunge, Jon A Beilstein J Org Chem Full Research Paper The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium π-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening. Beilstein-Institut 2012-07-27 /pmc/articles/PMC3458738/ /pubmed/23019448 http://dx.doi.org/10.3762/bjoc.8.133 Text en Copyright © 2012, Chattopadhyay et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Chattopadhyay, Kalicharan
Fenster, Erik
Grenning, Alexander J
Tunge, Jon A
Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles
title Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles
title_full Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles
title_fullStr Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles
title_full_unstemmed Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles
title_short Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles
title_sort palladium-catalyzed substitution of (coumarinyl)methyl acetates with c-, n-, and s-nucleophiles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458738/
https://www.ncbi.nlm.nih.gov/pubmed/23019448
http://dx.doi.org/10.3762/bjoc.8.133
work_keys_str_mv AT chattopadhyaykalicharan palladiumcatalyzedsubstitutionofcoumarinylmethylacetateswithcnandsnucleophiles
AT fenstererik palladiumcatalyzedsubstitutionofcoumarinylmethylacetateswithcnandsnucleophiles
AT grenningalexanderj palladiumcatalyzedsubstitutionofcoumarinylmethylacetateswithcnandsnucleophiles
AT tungejona palladiumcatalyzedsubstitutionofcoumarinylmethylacetateswithcnandsnucleophiles

Ejemplares similares