Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines

Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the c...

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Autores: Maestre Cera, Lourdes, Dorel, Ruth, Pablo, Óscar, Escofet, Imma, Sameera, W. M. C., Álvarez, Eleuterio, Maseras, Feliu, Díaz Requejo, María Mar, Echavarren, Antonio M., Pérez Romero, Pedro José
Tipo de recurso: artículo
Fecha de publicación:2017
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:10272/16191
Acceso en línea:http://hdl.handle.net/10272/16191
Access Level:acceso abierto
Palabra clave:Catalyst
Aminimides
Nitrene
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spelling Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to AminesMaestre Cera, LourdesDorel, RuthPablo, ÓscarEscofet, ImmaSameera, W. M. C.Álvarez, EleuterioMaseras, FeliuDíaz Requejo, María MarEchavarren, Antonio M.Pérez Romero, Pedro JoséCatalystAminimidesNitreneSilver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N formation were exclusively formed. Theoretical mechanistic studies have shown that this selective Namidation reaction proceeds through triplet silver-nitrenes.American Chemical Society20172017-01-0120172017-01-01journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10272/16191reponame: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:10272/161912026-06-02T14:58:11Z
dc.title.none.fl_str_mv Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
title Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
spellingShingle Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
Maestre Cera, Lourdes
Catalyst
Aminimides
Nitrene
title_short Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
title_full Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
title_fullStr Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
title_full_unstemmed Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
title_sort Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
dc.creator.none.fl_str_mv Maestre Cera, Lourdes
Dorel, Ruth
Pablo, Óscar
Escofet, Imma
Sameera, W. M. C.
Álvarez, Eleuterio
Maseras, Feliu
Díaz Requejo, María Mar
Echavarren, Antonio M.
Pérez Romero, Pedro José
author Maestre Cera, Lourdes
author_facet Maestre Cera, Lourdes
Dorel, Ruth
Pablo, Óscar
Escofet, Imma
Sameera, W. M. C.
Álvarez, Eleuterio
Maseras, Feliu
Díaz Requejo, María Mar
Echavarren, Antonio M.
Pérez Romero, Pedro José
author_role author
author2 Dorel, Ruth
Pablo, Óscar
Escofet, Imma
Sameera, W. M. C.
Álvarez, Eleuterio
Maseras, Feliu
Díaz Requejo, María Mar
Echavarren, Antonio M.
Pérez Romero, Pedro José
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv
dc.subject.none.fl_str_mv Catalyst
Aminimides
Nitrene
topic Catalyst
Aminimides
Nitrene
description Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N formation were exclusively formed. Theoretical mechanistic studies have shown that this selective Namidation reaction proceeds through triplet silver-nitrenes.
publishDate 2017
dc.date.none.fl_str_mv 2017
2017-01-01
2017
2017-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10272/16191
url http://hdl.handle.net/10272/16191
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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