Introducing 1,3-enyne functionalization by nitrene transfer reaction

In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report t...

Descripción completa

Detalles Bibliográficos
Autores: Rodriguez, Anabel M., Sciortino, Giuseppe, Munoz-Gutierrez, Lidia, Molina, Francisco, Maseras, Feliu, Diaz-Requejo, M. Mar, Perez, Pedro J.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2024
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/537495
Acceso en línea:http://hdl.handle.net/2072/537495
https://doi.org/10.1016/j.checat.2023.100865
Access Level:acceso abierto
Palabra clave:Química
54
id ES_3552f4e3e8c70a95307c377b34ddea98
oai_identifier_str oai:recercat.cat:2072/537495
network_acronym_str ES
network_name_str España
repository_id_str
spelling Introducing 1,3-enyne functionalization by nitrene transfer reactionRodriguez, Anabel M.Sciortino, GiuseppeMunoz-Gutierrez, LidiaMolina, FranciscoMaseras, FeliuDiaz-Requejo, M. MarPerez, Pedro J.Química54In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report the first example of this transformation, leading to the formation of propargyl aziridines or unsaturated sulfinamides, corresponding to the attack of a copper-nitrene intermediate onto the ene or yne sites. Density functional theory (DFT) studies have provided an explanation for this diverse reactivity, which is sustained on the interactions of the enyne substituent with the pyrazolyl rings of the trispyrazolylborate ancillary ligand of the catalyst.Cell-Press Elsevier2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion10 p.application/pdfhttp://hdl.handle.net/2072/537495https://doi.org/10.1016/j.checat.2023.100865RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésMinisterio de Ciencia e Innovación for Grants PID2020-113797RB-C21, PID2020-112825RB-I00, CES2019-000925-S and RED2022-134074-T.Junta de Andalucía (P20-00348), Universidad de Huelva (P.O.Feder UHU-202016)CERCA Programme/Generalitat de CatalunyaAMR thanks Ministerio de Universidades for a FPU fellowshipG.S. thanks MICINN Juan de la Cierva program, FJC2019-039135-ICC-BY-NC-ND licenseinfo:eu-repo/semantics/openAccessoai:recercat.cat:2072/5374952026-05-29T05:05:01Z
dc.title.none.fl_str_mv Introducing 1,3-enyne functionalization by nitrene transfer reaction
title Introducing 1,3-enyne functionalization by nitrene transfer reaction
spellingShingle Introducing 1,3-enyne functionalization by nitrene transfer reaction
Rodriguez, Anabel M.
Química
54
title_short Introducing 1,3-enyne functionalization by nitrene transfer reaction
title_full Introducing 1,3-enyne functionalization by nitrene transfer reaction
title_fullStr Introducing 1,3-enyne functionalization by nitrene transfer reaction
title_full_unstemmed Introducing 1,3-enyne functionalization by nitrene transfer reaction
title_sort Introducing 1,3-enyne functionalization by nitrene transfer reaction
dc.creator.none.fl_str_mv Rodriguez, Anabel M.
Sciortino, Giuseppe
Munoz-Gutierrez, Lidia
Molina, Francisco
Maseras, Feliu
Diaz-Requejo, M. Mar
Perez, Pedro J.
author Rodriguez, Anabel M.
author_facet Rodriguez, Anabel M.
Sciortino, Giuseppe
Munoz-Gutierrez, Lidia
Molina, Francisco
Maseras, Feliu
Diaz-Requejo, M. Mar
Perez, Pedro J.
author_role author
author2 Sciortino, Giuseppe
Munoz-Gutierrez, Lidia
Molina, Francisco
Maseras, Feliu
Diaz-Requejo, M. Mar
Perez, Pedro J.
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
54
topic Química
54
description In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report the first example of this transformation, leading to the formation of propargyl aziridines or unsaturated sulfinamides, corresponding to the attack of a copper-nitrene intermediate onto the ene or yne sites. Density functional theory (DFT) studies have provided an explanation for this diverse reactivity, which is sustained on the interactions of the enyne substituent with the pyrazolyl rings of the trispyrazolylborate ancillary ligand of the catalyst.
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/537495
https://doi.org/10.1016/j.checat.2023.100865
url http://hdl.handle.net/2072/537495
https://doi.org/10.1016/j.checat.2023.100865
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Ministerio de Ciencia e Innovación for Grants PID2020-113797RB-C21, PID2020-112825RB-I00, CES2019-000925-S and RED2022-134074-T.
Junta de Andalucía (P20-00348), Universidad de Huelva (P.O.Feder UHU-202016)
CERCA Programme/Generalitat de Catalunya
AMR thanks Ministerio de Universidades for a FPU fellowship
G.S. thanks MICINN Juan de la Cierva program, FJC2019-039135-I
dc.rights.none.fl_str_mv CC-BY-NC-ND license
info:eu-repo/semantics/openAccess
rights_invalid_str_mv CC-BY-NC-ND license
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 10 p.
application/pdf
dc.publisher.none.fl_str_mv Cell-Press Elsevier
publisher.none.fl_str_mv Cell-Press Elsevier
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869405874352553984
score 15,812429

Similares en LA Referencia