Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes

A palladium‐catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes leading to tetrahydroisoquinolin‐4‐ols is reported. A variety of products were isolated in good to excellent yields. The joint experimental‐computational study shows that although two competitive reaction pathway...

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Autores: Solé Arjó, Daniel, Mariani, Francesco, Fernández Cadenas, Israel
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2014
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/127725
Acceso en línea:https://hdl.handle.net/2445/127725
Access Level:acceso abierto
Palabra clave:Catàlisi
Compostos cíclics
Teoria del funcional de densitat
Pal·ladi (Element químic)
Catalysis
Cyclic compounds
Density functionals
Palladium
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spelling Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydesSolé Arjó, DanielMariani, FrancescoFernández Cadenas, IsraelCatàlisiCompostos cíclicsTeoria del funcional de densitatPal·ladi (Element químic)CatalysisCyclic compoundsDensity functionalsPalladiumA palladium‐catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes leading to tetrahydroisoquinolin‐4‐ols is reported. A variety of products were isolated in good to excellent yields. The joint experimental‐computational study shows that although two competitive reaction pathways can be promoted by Pd(0) starting from α‐(2‐iodobenzylamino)‐aldehydes, the selectivity of the process can be controlled by the proper selection of the base. While the nucleophilic addition of the aryl‐Pd(II) intermediate to the carbonyl group is selectively promoted by using the base triethylamine (Et3N), the CH bond activation at the formyl group competes with the nucleophilic addition only when the base is replaced by cesium carbonate (Cs2CO3). Keywords: catalysis; cyclization; density functional theory (DFT) calculations; nucleophilic addition; palladiumWiley-VCH2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/127725Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1002/adsc.201400408Advanced Synthesis & Catalysis, 2014, vol. 356, num. 14-15, p. 3237-3243https://doi.org/10.1002/adsc.201400408(c) Wiley-VCH, 2014info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1277252026-05-27T06:46:51Z
dc.title.none.fl_str_mv Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
title Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
spellingShingle Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
Solé Arjó, Daniel
Catàlisi
Compostos cíclics
Teoria del funcional de densitat
Pal·ladi (Element químic)
Catalysis
Cyclic compounds
Density functionals
Palladium
title_short Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
title_full Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
title_fullStr Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
title_full_unstemmed Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
title_sort Synthesis of isoquinolin-4-ols by palladium-catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes
dc.creator.none.fl_str_mv Solé Arjó, Daniel
Mariani, Francesco
Fernández Cadenas, Israel
author Solé Arjó, Daniel
author_facet Solé Arjó, Daniel
Mariani, Francesco
Fernández Cadenas, Israel
author_role author
author2 Mariani, Francesco
Fernández Cadenas, Israel
author2_role author
author
dc.subject.none.fl_str_mv Catàlisi
Compostos cíclics
Teoria del funcional de densitat
Pal·ladi (Element químic)
Catalysis
Cyclic compounds
Density functionals
Palladium
topic Catàlisi
Compostos cíclics
Teoria del funcional de densitat
Pal·ladi (Element químic)
Catalysis
Cyclic compounds
Density functionals
Palladium
description A palladium‐catalysed intramolecular nucleophilic addition of aryl iodides to aldehydes leading to tetrahydroisoquinolin‐4‐ols is reported. A variety of products were isolated in good to excellent yields. The joint experimental‐computational study shows that although two competitive reaction pathways can be promoted by Pd(0) starting from α‐(2‐iodobenzylamino)‐aldehydes, the selectivity of the process can be controlled by the proper selection of the base. While the nucleophilic addition of the aryl‐Pd(II) intermediate to the carbonyl group is selectively promoted by using the base triethylamine (Et3N), the CH bond activation at the formyl group competes with the nucleophilic addition only when the base is replaced by cesium carbonate (Cs2CO3). Keywords: catalysis; cyclization; density functional theory (DFT) calculations; nucleophilic addition; palladium
publishDate 2014
dc.date.none.fl_str_mv 2014
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/127725
url https://hdl.handle.net/2445/127725
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1002/adsc.201400408
Advanced Synthesis & Catalysis, 2014, vol. 356, num. 14-15, p. 3237-3243
https://doi.org/10.1002/adsc.201400408
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2014
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2014
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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