Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions

The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5‐tribromo‐pyrazolyl)borate). N‐substituted pyrroles...

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Detalles Bibliográficos
Autores: Moreno Rodríguez, Anabel, Ramírez Rodríguez, Manuel, Díaz Requejo, María Mar, Pérez Romero, Pedro José
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Universidad de Huelva (UHU)
Repositorio:Arias Montano. Repositorio Institucional de la Universidad de Huelva
Idioma:inglés
OAI Identifier:oai:ariasmontano.uhu.es:10272/19698
Acceso en línea:http://hdl.handle.net/10272/19698
Access Level:acceso abierto
Palabra clave:Nitrene transfer
Pyrrole functionalization
C-H amidation
Copper catalysis
Copper nitrene
23 Química
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spelling Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer ReactionsMoreno Rodríguez, AnabelRamírez Rodríguez, ManuelDíaz Requejo, María MarPérez Romero, Pedro JoséNitrene transferPyrrole functionalizationC-H amidationCopper catalysisCopper nitrene23 QuímicaThe catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5‐tribromo‐pyrazolyl)borate). N‐substituted pyrroles also verify the same transformation. The mechanism proposal is similar to that previously described for benzene amidation with the same catalyst and PhI=NTs, which takes place through aziridine formation, ring opening and 1,2‐hydrogen shift. A cascade reaction involving the coupling of 2,5‐dimethylfuran, 1,2,3‐trimethyl‐pyrrole and a nitrene NTs group is also described, leading to a 1,2‐dihydropyridine‐imine compound.Wiley-VCH Verlag20202020-03-0120202020-03-01journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10272/19698reponame:Arias Montano. Repositorio Institucional de la Universidad de Huelvainstname:Universidad de Huelva (UHU)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Atribución-NoComercial-SinDerivadas 3.0 Españahttp://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccessoai:ariasmontano.uhu.es:10272/196982026-06-02T14:58:11Z
dc.title.none.fl_str_mv Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
title Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
spellingShingle Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
Moreno Rodríguez, Anabel
Nitrene transfer
Pyrrole functionalization
C-H amidation
Copper catalysis
Copper nitrene
23 Química
title_short Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
title_full Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
title_fullStr Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
title_full_unstemmed Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
title_sort Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
dc.creator.none.fl_str_mv Moreno Rodríguez, Anabel
Ramírez Rodríguez, Manuel
Díaz Requejo, María Mar
Pérez Romero, Pedro José
author Moreno Rodríguez, Anabel
author_facet Moreno Rodríguez, Anabel
Ramírez Rodríguez, Manuel
Díaz Requejo, María Mar
Pérez Romero, Pedro José
author_role author
author2 Ramírez Rodríguez, Manuel
Díaz Requejo, María Mar
Pérez Romero, Pedro José
author2_role author
author
author
dc.contributor.none.fl_str_mv
dc.subject.none.fl_str_mv Nitrene transfer
Pyrrole functionalization
C-H amidation
Copper catalysis
Copper nitrene
23 Química
topic Nitrene transfer
Pyrrole functionalization
C-H amidation
Copper catalysis
Copper nitrene
23 Química
description The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5‐tribromo‐pyrazolyl)borate). N‐substituted pyrroles also verify the same transformation. The mechanism proposal is similar to that previously described for benzene amidation with the same catalyst and PhI=NTs, which takes place through aziridine formation, ring opening and 1,2‐hydrogen shift. A cascade reaction involving the coupling of 2,5‐dimethylfuran, 1,2,3‐trimethyl‐pyrrole and a nitrene NTs group is also described, leading to a 1,2‐dihydropyridine‐imine compound.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020-03-01
2020
2020-03-01
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/10272/19698
url http://hdl.handle.net/10272/19698
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución-NoComercial-SinDerivadas 3.0 España
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
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
Atribución-NoComercial-SinDerivadas 3.0 España
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH Verlag
publisher.none.fl_str_mv Wiley-VCH Verlag
dc.source.none.fl_str_mv reponame:Arias Montano. Repositorio Institucional de la Universidad de Huelva
instname:Universidad de Huelva (UHU)
instname_str Universidad de Huelva (UHU)
reponame_str Arias Montano. Repositorio Institucional de la Universidad de Huelva
collection Arias Montano. Repositorio Institucional de la Universidad de Huelva
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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