Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes

Mesoionic 4,4'-bis(1,2,3-triazole-5,5'-diylidene) Rh(I) complexes having a C2 chiral 4,4'-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC....

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Autores: Aizpurua, Jesús M., Sagartzazu-Aizpurua, Maialen, Monasterio, Zaira, Azcune, Itxaso, Mendicute, Claudio, Miranda, José Ignacio, García-Lecina, Eva, Altube, Ainhoa, Fratila, Raluca M.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2012
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/344031
Acceso en línea:http://hdl.handle.net/10261/344031
Access Level:acceso abierto
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spelling Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenesAizpurua, Jesús M.Sagartzazu-Aizpurua, MaialenMonasterio, ZairaAzcune, ItxasoMendicute, ClaudioMiranda, José IgnacioGarcía-Lecina, EvaAltube, AinhoaFratila, Raluca M.Mesoionic 4,4'-bis(1,2,3-triazole-5,5'-diylidene) Rh(I) complexes having a C2 chiral 4,4'-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.This work was supported by the Ministerio de Ciencia e Innovación (MICINN, Spain) (Project: CTQ2010-21625-C02-01), UPV/EHU, and Gobierno Vasco (ETORTEK-nanoIKER IE-11/304). We thank SGIker UPV/EHU for NMR and X-ray crystallography facilities. Grants from Gobierno Vasco to M.S.A. and UPV/EHU to Z.M. are acknowledged.Peer reviewedAmerican Chemical SocietyMinisterio de Ciencia e Innovación (España)Eusko JaurlaritzaUniversidad del País Vasco202420242012info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10261/344031reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MICINN//CTQ2010-21625-C02-01Aizpurua, Javier; Sagartzazu-Aizpurua, Maialen; Monasterio, Zaira; Azcune, Itxaso; Mendicute, Claudio; Miranda, José Ignacio; García-Lecina, Eva; Altube, Ainhoa; Fratila, Raluca M.; 2012; Supporting Information for Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes [Dataset]; American Chemical Society; https://doi.org/10.1021/ol3004657https://doi.org/10.1021/ol3004657Noinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3440312026-05-22T06:33:51Z
dc.title.none.fl_str_mv Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
title Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
spellingShingle Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
Aizpurua, Jesús M.
title_short Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
title_full Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
title_fullStr Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
title_full_unstemmed Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
title_sort Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes
dc.creator.none.fl_str_mv Aizpurua, Jesús M.
Sagartzazu-Aizpurua, Maialen
Monasterio, Zaira
Azcune, Itxaso
Mendicute, Claudio
Miranda, José Ignacio
García-Lecina, Eva
Altube, Ainhoa
Fratila, Raluca M.
author Aizpurua, Jesús M.
author_facet Aizpurua, Jesús M.
Sagartzazu-Aizpurua, Maialen
Monasterio, Zaira
Azcune, Itxaso
Mendicute, Claudio
Miranda, José Ignacio
García-Lecina, Eva
Altube, Ainhoa
Fratila, Raluca M.
author_role author
author2 Sagartzazu-Aizpurua, Maialen
Monasterio, Zaira
Azcune, Itxaso
Mendicute, Claudio
Miranda, José Ignacio
García-Lecina, Eva
Altube, Ainhoa
Fratila, Raluca M.
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
Eusko Jaurlaritza
Universidad del País Vasco
description Mesoionic 4,4'-bis(1,2,3-triazole-5,5'-diylidene) Rh(I) complexes having a C2 chiral 4,4'-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.
publishDate 2012
dc.date.none.fl_str_mv 2012
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/344031
url http://hdl.handle.net/10261/344031
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MICINN//CTQ2010-21625-C02-01
Aizpurua, Javier; Sagartzazu-Aizpurua, Maialen; Monasterio, Zaira; Azcune, Itxaso; Mendicute, Claudio; Miranda, José Ignacio; García-Lecina, Eva; Altube, Ainhoa; Fratila, Raluca M.; 2012; Supporting Information for Introducing axial chirality into mesoionic 4,4’-bis(1,2,3-triazole) dicarbenes [Dataset]; American Chemical Society; https://doi.org/10.1021/ol3004657
https://doi.org/10.1021/ol3004657
No
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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