Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand

A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3-bis(2-6-diisopropylphenyl)imidazolidin-2-ylidene) de...

Descripción completa

Detalles Bibliográficos
Autores principales: Schmid, Thibault E, Modicom, Florian, Dumas, Adrien, Borré, Etienne, Toupet, Loic, Baslé, Olivier, Mauduit, Marc
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578404/
https://www.ncbi.nlm.nih.gov/pubmed/26425213
http://dx.doi.org/10.3762/bjoc.11.169
_version_ 1782391112918368256
author Schmid, Thibault E
Modicom, Florian
Dumas, Adrien
Borré, Etienne
Toupet, Loic
Baslé, Olivier
Mauduit, Marc
author_facet Schmid, Thibault E
Modicom, Florian
Dumas, Adrien
Borré, Etienne
Toupet, Loic
Baslé, Olivier
Mauduit, Marc
author_sort Schmid, Thibault E
collection PubMed
description A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3-bis(2-6-diisopropylphenyl)imidazolidin-2-ylidene) demonstrated excellent latent behaviour in ring closing metathesis (RCM) reaction and could be activated in the presence of a Brønsted acid. The versatility of the catalyst 4a was subsequently demonstrated in RCM, cross-metathesis (CM) and enyne metathesis reactions.
format Online
Article
Text
id pubmed-4578404
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-45784042015-09-30 Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand Schmid, Thibault E Modicom, Florian Dumas, Adrien Borré, Etienne Toupet, Loic Baslé, Olivier Mauduit, Marc Beilstein J Org Chem Full Research Paper A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3-bis(2-6-diisopropylphenyl)imidazolidin-2-ylidene) demonstrated excellent latent behaviour in ring closing metathesis (RCM) reaction and could be activated in the presence of a Brønsted acid. The versatility of the catalyst 4a was subsequently demonstrated in RCM, cross-metathesis (CM) and enyne metathesis reactions. Beilstein-Institut 2015-09-03 /pmc/articles/PMC4578404/ /pubmed/26425213 http://dx.doi.org/10.3762/bjoc.11.169 Text en Copyright © 2015, Schmid et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Schmid, Thibault E
Modicom, Florian
Dumas, Adrien
Borré, Etienne
Toupet, Loic
Baslé, Olivier
Mauduit, Marc
Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
title Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
title_full Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
title_fullStr Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
title_full_unstemmed Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
title_short Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand
title_sort latent ruthenium–indenylidene catalysts bearing a n-heterocyclic carbene and a bidentate picolinate ligand
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578404/
https://www.ncbi.nlm.nih.gov/pubmed/26425213
http://dx.doi.org/10.3762/bjoc.11.169
work_keys_str_mv AT schmidthibaulte latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand
AT modicomflorian latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand
AT dumasadrien latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand
AT borreetienne latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand
AT toupetloic latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand
AT basleolivier latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand
AT mauduitmarc latentrutheniumindenylidenecatalystsbearinganheterocycliccarbeneandabidentatepicolinateligand

Ejemplares similares