Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand

The chiral tetradentate N4-donor ligand, 1-methyl-2-({(S)-2-[(S)-1-(1-methylbenzimidazol-2-yl methyl)pyrrolidin-2-yl]pyrrolidin-1-yl}methyl) benzimidazole (S,S-PDBzL), based on a chiral dipyrrolidine backbone, has been synthesized and its corresponding Fe(II) complex has been prepared and characteri...

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Detalhes bibliográficos
Autores: Mitra, Mainak, Cussó Forest, Olaf, Bhat, Satish S., Sun, Mingzhe, Cianfanelli, Marco, Costas Salgueiro, Miquel, Nordlander, Ebbe
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2019
País:España
Recursos: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:10256/18185
Acesso em linha:http://hdl.handle.net/10256/18185
Access Level:acceso abierto
Palavra-chave:Alquens -- Oxidació
Alkenes -- Oxidation
Catalitzadors
Catalysts
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spelling Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligandMitra, MainakCussó Forest, OlafBhat, Satish S.Sun, MingzheCianfanelli, MarcoCostas Salgueiro, MiquelNordlander, EbbeAlquens -- OxidacióAlkenes -- OxidationCatalitzadorsCatalystsThe chiral tetradentate N4-donor ligand, 1-methyl-2-({(S)-2-[(S)-1-(1-methylbenzimidazol-2-yl methyl)pyrrolidin-2-yl]pyrrolidin-1-yl}methyl) benzimidazole (S,S-PDBzL), based on a chiral dipyrrolidine backbone, has been synthesized and its corresponding Fe(II) complex has been prepared and characterized. The X-ray structure of the complex reveals that the Fe(II) ion is in a distorted octahedral coordination environment with two cis-oriented coordination sites occupied by (labile) triflate anions. The ability of the iron complex to catalyze asymmetric epoxidation reactions of olefins with H2O2 was investigated, using 2-cyclohexen-1-one, 2-cyclopenten-1-one, cis-β-methylstyrene, isophorone, chalcones and tetralones as substrates. Different carboxylic acids were used as additives to enhance yields and enantioselectivities, and 2-ethylhexanoic acid was found to give the best results. The catalysis results indicate that the Fe(II) complex is capable of effecting comparatively high enantioselectivities (>80%) in the epoxidation reactionsThe research has been carried out within the frameworks of the International Research Training Group Metal sites in biomolecules: structures, regulation and mechanisms (http://www.biometals.eu), the Marie Sklodowska-Curie Innovative Training Network MSCAITN-2015-ETN 675020 and COST Action CM1003. M. M. thanks the European Commission for an Erasmus Mundus fellowshipRoyal Society of Chemistry (RSC)2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewedapplication/pdfhttp://hdl.handle.net/10256/18185http://hdl.handle.net/10256/18185Dalton Transactions, 2019, vol. 48, p. 6123-6131Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C8DT04449Jinfo:eu-repo/semantics/altIdentifier/issn/1477-9226info:eu-repo/semantics/altIdentifier/eissn/1477-9234info:eu-repo/grantAgreement/EC/H2020/675020Attribution-NonCommercial 4.0 Internationalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/181852026-05-29T05:05:01Z
dc.title.none.fl_str_mv Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
title Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
spellingShingle Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
Mitra, Mainak
Alquens -- Oxidació
Alkenes -- Oxidation
Catalitzadors
Catalysts
title_short Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
title_full Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
title_fullStr Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
title_full_unstemmed Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
title_sort Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand
dc.creator.none.fl_str_mv Mitra, Mainak
Cussó Forest, Olaf
Bhat, Satish S.
Sun, Mingzhe
Cianfanelli, Marco
Costas Salgueiro, Miquel
Nordlander, Ebbe
author Mitra, Mainak
author_facet Mitra, Mainak
Cussó Forest, Olaf
Bhat, Satish S.
Sun, Mingzhe
Cianfanelli, Marco
Costas Salgueiro, Miquel
Nordlander, Ebbe
author_role author
author2 Cussó Forest, Olaf
Bhat, Satish S.
Sun, Mingzhe
Cianfanelli, Marco
Costas Salgueiro, Miquel
Nordlander, Ebbe
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Alquens -- Oxidació
Alkenes -- Oxidation
Catalitzadors
Catalysts
topic Alquens -- Oxidació
Alkenes -- Oxidation
Catalitzadors
Catalysts
description The chiral tetradentate N4-donor ligand, 1-methyl-2-({(S)-2-[(S)-1-(1-methylbenzimidazol-2-yl methyl)pyrrolidin-2-yl]pyrrolidin-1-yl}methyl) benzimidazole (S,S-PDBzL), based on a chiral dipyrrolidine backbone, has been synthesized and its corresponding Fe(II) complex has been prepared and characterized. The X-ray structure of the complex reveals that the Fe(II) ion is in a distorted octahedral coordination environment with two cis-oriented coordination sites occupied by (labile) triflate anions. The ability of the iron complex to catalyze asymmetric epoxidation reactions of olefins with H2O2 was investigated, using 2-cyclohexen-1-one, 2-cyclopenten-1-one, cis-β-methylstyrene, isophorone, chalcones and tetralones as substrates. Different carboxylic acids were used as additives to enhance yields and enantioselectivities, and 2-ethylhexanoic acid was found to give the best results. The catalysis results indicate that the Fe(II) complex is capable of effecting comparatively high enantioselectivities (>80%) in the epoxidation reactions
publishDate 2019
dc.date.none.fl_str_mv 2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/18185
http://hdl.handle.net/10256/18185
url http://hdl.handle.net/10256/18185
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/C8DT04449J
info:eu-repo/semantics/altIdentifier/issn/1477-9226
info:eu-repo/semantics/altIdentifier/eissn/1477-9234
info:eu-repo/grantAgreement/EC/H2020/675020
dc.rights.none.fl_str_mv Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
dc.source.none.fl_str_mv Dalton Transactions, 2019, vol. 48, p. 6123-6131
Articles publicats (D-Q)
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
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score 15.812455

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