Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines

A protocol for the Pd(II)-catalyzed C-H alkenylation reaction of substituted N-allylanilines via an unusual 6-endo process has been developed. A DFT study of the mechanistic pathway has shown that the coordination of the remote protecting group to the palladium center is determinant for the control...

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Autores: Carral Menoyo, Asier, Sotorríos Manrique, Lia, Ortiz de Elguea Flecha, Verónica, Díaz Andrés, Aitor, Sotomayor Anduiza, María Nuria, Gómez Bengoa, Enrique, Lete Expósito, María Esther
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/63117
Acceso en línea:http://hdl.handle.net/10810/63117
Access Level:acceso abierto
Palabra clave:palladium
C-H alkenylation
quinolines
DFT calculations
cyclization
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spelling Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolinesCarral Menoyo, AsierSotorríos Manrique, LiaOrtiz de Elguea Flecha, VerónicaDíaz Andrés, AitorSotomayor Anduiza, María NuriaGómez Bengoa, EnriqueLete Expósito, María EstherpalladiumC-H alkenylationquinolinesDFT calculationscyclizationA protocol for the Pd(II)-catalyzed C-H alkenylation reaction of substituted N-allylanilines via an unusual 6-endo process has been developed. A DFT study of the mechanistic pathway has shown that the coordination of the remote protecting group to the palladium center is determinant for the control of the regioselectivity in favor of the 6-endo process. The reaction would proceed via prior activation of the alkene. This procedure constitutes a mild and efficient method for the synthesis of 1,4- dihydroquinoline derivatives from simple and readily accessible substrates.Ministerio de Economía y Competitividad (CTQ2016-74881-P; CTQ2016-78083-P) // Gobierno Vasco (IT1045-16)American Chemical Society202320232019info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/63117reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MINECO/CTQ2016-74881-P/info:eu-repo/grantAgreement/MINECO/CTQ2016-78083-P/https://pubs.acs.org/doi/10.1021/acs.joc.9b03174https://doi.org/10.1021/acs.joc.9b03174info:eu-repo/semantics/openAccess© 2019, American Chemical Societyoai:addi.ehu.eus:10810/631172026-06-18T09:23:17Z
dc.title.none.fl_str_mv Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
title Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
spellingShingle Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
Carral Menoyo, Asier
palladium
C-H alkenylation
quinolines
DFT calculations
cyclization
title_short Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
title_full Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
title_fullStr Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
title_full_unstemmed Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
title_sort Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group. Mechanistic insight and application to the synthesis of dihydroquinolines
dc.creator.none.fl_str_mv Carral Menoyo, Asier
Sotorríos Manrique, Lia
Ortiz de Elguea Flecha, Verónica
Díaz Andrés, Aitor
Sotomayor Anduiza, María Nuria
Gómez Bengoa, Enrique
Lete Expósito, María Esther
author Carral Menoyo, Asier
author_facet Carral Menoyo, Asier
Sotorríos Manrique, Lia
Ortiz de Elguea Flecha, Verónica
Díaz Andrés, Aitor
Sotomayor Anduiza, María Nuria
Gómez Bengoa, Enrique
Lete Expósito, María Esther
author_role author
author2 Sotorríos Manrique, Lia
Ortiz de Elguea Flecha, Verónica
Díaz Andrés, Aitor
Sotomayor Anduiza, María Nuria
Gómez Bengoa, Enrique
Lete Expósito, María Esther
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv palladium
C-H alkenylation
quinolines
DFT calculations
cyclization
topic palladium
C-H alkenylation
quinolines
DFT calculations
cyclization
description A protocol for the Pd(II)-catalyzed C-H alkenylation reaction of substituted N-allylanilines via an unusual 6-endo process has been developed. A DFT study of the mechanistic pathway has shown that the coordination of the remote protecting group to the palladium center is determinant for the control of the regioselectivity in favor of the 6-endo process. The reaction would proceed via prior activation of the alkene. This procedure constitutes a mild and efficient method for the synthesis of 1,4- dihydroquinoline derivatives from simple and readily accessible substrates.
publishDate 2019
dc.date.none.fl_str_mv 2019
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/63117
url http://hdl.handle.net/10810/63117
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MINECO/CTQ2016-74881-P/
info:eu-repo/grantAgreement/MINECO/CTQ2016-78083-P/
https://pubs.acs.org/doi/10.1021/acs.joc.9b03174
https://doi.org/10.1021/acs.joc.9b03174
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
© 2019, American Chemical Society
eu_rights_str_mv openAccess
rights_invalid_str_mv © 2019, American Chemical Society
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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