Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds

Cycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of C(sp3)–H bonds an...

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Autores: Vidal Pereira, Xandro, Mascareñas Cid, José Luis, Gulías Costa, Moisés
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad de Santiago de Compostela (USC)
Repositorio:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Idioma:inglés
OAI Identifier:oai:minerva.usc.gal:10347/26594
Acceso en línea:http://hdl.handle.net/10347/26594
Access Level:acceso abierto
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spelling Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H BondsVidal Pereira, XandroMascareñas Cid, José LuisGulías Costa, MoisésCycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of C(sp3)–H bonds and provides a direct, unconventional entry to tetrahydroquinoline skeletons. The reaction utilizes amidotolyl precursors and allenes as annulation partners, and is catalyzed by Pd(II) precursors in combination with specific N-acetylated amino acid ligands. The reactivity can be extended to ortho-methyl benzylamides, which provide for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation procesAmerican Chemical SocietyUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais MolecularesUniversidade de Santiago de Compostela. Departamento de Química Orgánica20212021-01-0120212021-01-01journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10347/26594reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostelainstname:Universidad de Santiago de Compostela (USC)InglésengEuropean Commission http://dx.doi.org/10.13039/501100000780 Seventh Framework Programme 340055Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2016-76689-RAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-108624RB-I00 HERRAMIENTAS BASADAS EN METALES PARA SU USO EN QUIMICA BIOLOGICA Y BIOMEDICINA. DESARROLLO DE NUEVAS ESTRATEGIAS ANTICANCERMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2016-77047-PAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-110385GB-I00 NUEVOS METODOS DE SINTESIS QUIMICA MEDIANTE LA FUNCIONALIZACION DE ENLACES C-H CON CATALIZADORES METALICOSMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2016-81797-REDCopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:minerva.usc.gal:10347/265942026-06-15T12:47:27Z
dc.title.none.fl_str_mv Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
title Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
spellingShingle Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
Vidal Pereira, Xandro
title_short Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
title_full Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
title_fullStr Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
title_full_unstemmed Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
title_sort Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds
dc.creator.none.fl_str_mv Vidal Pereira, Xandro
Mascareñas Cid, José Luis
Gulías Costa, Moisés
author Vidal Pereira, Xandro
author_facet Vidal Pereira, Xandro
Mascareñas Cid, José Luis
Gulías Costa, Moisés
author_role author
author2 Mascareñas Cid, José Luis
Gulías Costa, Moisés
author2_role author
author
dc.contributor.none.fl_str_mv Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
Universidade de Santiago de Compostela. Departamento de Química Orgánica
description Cycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of C(sp3)–H bonds and provides a direct, unconventional entry to tetrahydroquinoline skeletons. The reaction utilizes amidotolyl precursors and allenes as annulation partners, and is catalyzed by Pd(II) precursors in combination with specific N-acetylated amino acid ligands. The reactivity can be extended to ortho-methyl benzylamides, which provide for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation proces
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-01-01
2021
2021-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10347/26594
url http://hdl.handle.net/10347/26594
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv European Commission http://dx.doi.org/10.13039/501100000780 Seventh Framework Programme 340055
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2016-76689-R
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-108624RB-I00 HERRAMIENTAS BASADAS EN METALES PARA SU USO EN QUIMICA BIOLOGICA Y BIOMEDICINA. DESARROLLO DE NUEVAS ESTRATEGIAS ANTICANCER
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2016-77047-P
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-110385GB-I00 NUEVOS METODOS DE SINTESIS QUIMICA MEDIANTE LA FUNCIONALIZACION DE ENLACES C-H CON CATALIZADORES METALICOS
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2016-81797-REDC
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
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:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
instname:Universidad de Santiago de Compostela (USC)
instname_str Universidad de Santiago de Compostela (USC)
reponame_str Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
collection Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
repository.name.fl_str_mv
repository.mail.fl_str_mv
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