Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction

1H‐Pyrroles can be directly functionalized by means of the incorporation of carbene groups from diazo compounds, in a process catalyzed by TpxCu complexes (Tpx=hydrotrispyrazolylborate ligand). The reactions take place with a complete selectivity toward the formal insertion of the carbene into the C...

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Detalles Bibliográficos
Autores: Moreno Rodríguez, Anabel, Molina González, Francisco, 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:10272/19646
Acceso en línea:http://hdl.handle.net/10272/19646
Access Level:acceso abierto
Palabra clave:Pyrrole functionalization
Copper catalysis
Carbene transfer
Diazo compounds
C-H functionalization
Selectivity
23 Química
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spelling Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer ReactionMoreno Rodríguez, AnabelMolina González, FranciscoDíaz Requejo, María MarPérez Romero, Pedro JoséPyrrole functionalizationCopper catalysisCarbene transferDiazo compoundsC-H functionalizationSelectivity23 Química1H‐Pyrroles can be directly functionalized by means of the incorporation of carbene groups from diazo compounds, in a process catalyzed by TpxCu complexes (Tpx=hydrotrispyrazolylborate ligand). The reactions take place with a complete selectivity toward the formal insertion of the carbene into the Cα−H bond, leading to alkylated pyrroles, with no modification of the Cβ−H, N−H or C=C bonds of the pyrrole unit. Alkyl substituents at C‐ring as well as alkyl, aryl, allyl or alkyne substitution at N atom are tolerated, the strategy affording 20 new pyrrole derivatives. The observance of partial deuteration at the methylene group when the reaction is carried out with added D2O serves to discard the direct insertion of the carbene group into the Csp2−H bond, the alternative electrophilic attack to the pyrrole ring being feasible.Wiley20202020-02-0120202020-02-01journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10272/19646reponame:Arias Montano. Repositorio Institucional de la Universidad de Huelvainstname:Universidad de Huelva (UHU)InglésengMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Not available Not availableopen 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:10272/196462026-06-02T14:58:11Z
dc.title.none.fl_str_mv Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
title Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
spellingShingle Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
Moreno Rodríguez, Anabel
Pyrrole functionalization
Copper catalysis
Carbene transfer
Diazo compounds
C-H functionalization
Selectivity
23 Química
title_short Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
title_full Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
title_fullStr Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
title_full_unstemmed Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
title_sort Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
dc.creator.none.fl_str_mv Moreno Rodríguez, Anabel
Molina González, Francisco
Díaz Requejo, María Mar
Pérez Romero, Pedro José
author Moreno Rodríguez, Anabel
author_facet Moreno Rodríguez, Anabel
Molina González, Francisco
Díaz Requejo, María Mar
Pérez Romero, Pedro José
author_role author
author2 Molina González, Francisco
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 Pyrrole functionalization
Copper catalysis
Carbene transfer
Diazo compounds
C-H functionalization
Selectivity
23 Química
topic Pyrrole functionalization
Copper catalysis
Carbene transfer
Diazo compounds
C-H functionalization
Selectivity
23 Química
description 1H‐Pyrroles can be directly functionalized by means of the incorporation of carbene groups from diazo compounds, in a process catalyzed by TpxCu complexes (Tpx=hydrotrispyrazolylborate ligand). The reactions take place with a complete selectivity toward the formal insertion of the carbene into the Cα−H bond, leading to alkylated pyrroles, with no modification of the Cβ−H, N−H or C=C bonds of the pyrrole unit. Alkyl substituents at C‐ring as well as alkyl, aryl, allyl or alkyne substitution at N atom are tolerated, the strategy affording 20 new pyrrole derivatives. The observance of partial deuteration at the methylene group when the reaction is carried out with added D2O serves to discard the direct insertion of the carbene group into the Csp2−H bond, the alternative electrophilic attack to the pyrrole ring being feasible.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020-02-01
2020
2020-02-01
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/10272/19646
url http://hdl.handle.net/10272/19646
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Not available Not available
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
publisher.none.fl_str_mv Wiley
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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