Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.21/12744 |
Resumo: | Two piano-stool iron(II) complexes bearing N-heterocyclic carbene ligands outfitted with acetamide- and amine-pendant arms [Cp*Fe(NHC(R))(CO)I] {Cp* = eta(5)-tetramethylcyclopentadienyl; R = CH2CONEt2(3), (CH2)(2)NEt2(4)}, have been prepared and fully characterized. Their catalytic activity in transfer hydrogenation (TH) of ketones usingiPrOH as a hydrogen source and catalytic amounts of base (LiOtBu) has been explored, along with that of previously reported [CpFe(NHC(R))(CO)I] {R =nBu (5), (CH2)(2)OH (6), Et (7), and (CH2)(3)OH (8)} complexes containing hydroxyl and nonfunctionalized alkyl arms. Complex3displayed the highest catalytic activity of the whole series3-8, reaching a TOF(50)value of 533 h(-1). NMR monitoring of the stoichiometric reaction of3with LiOtBu, allowed the identification of a new species3'containing a deprotonated amidate moiety, which has been fully characterized by(1)H,C-13, and(15)N NMR. Finally, a green protocol for the reduction of ketones through TH using glycerol as a hydrogen source, under microwave irradiation in the presence of catalytic amounts of3and base has been developed. |
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Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactionsCarbene ligandsTransfer hydrogenationReductionKetonesMicrowave irradiationTwo piano-stool iron(II) complexes bearing N-heterocyclic carbene ligands outfitted with acetamide- and amine-pendant arms [Cp*Fe(NHC(R))(CO)I] {Cp* = eta(5)-tetramethylcyclopentadienyl; R = CH2CONEt2(3), (CH2)(2)NEt2(4)}, have been prepared and fully characterized. Their catalytic activity in transfer hydrogenation (TH) of ketones usingiPrOH as a hydrogen source and catalytic amounts of base (LiOtBu) has been explored, along with that of previously reported [CpFe(NHC(R))(CO)I] {R =nBu (5), (CH2)(2)OH (6), Et (7), and (CH2)(3)OH (8)} complexes containing hydroxyl and nonfunctionalized alkyl arms. Complex3displayed the highest catalytic activity of the whole series3-8, reaching a TOF(50)value of 533 h(-1). NMR monitoring of the stoichiometric reaction of3with LiOtBu, allowed the identification of a new species3'containing a deprotonated amidate moiety, which has been fully characterized by(1)H,C-13, and(15)N NMR. Finally, a green protocol for the reduction of ketones through TH using glycerol as a hydrogen source, under microwave irradiation in the presence of catalytic amounts of3and base has been developed.Wiley Online LibraryRCIPLLopes, RitaRaya-Baron, AlvaroRobalo, M. PaulaS. Vinagreiro, CarolinaBarroso, SoniaRomão, Maria JoãoFernandez, IgnacioPereira, Mariette M.Royo2021-02-01T18:12:14Z2021-01-082021-01-08T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.21/12744engLOPES, Rita; [et al] – Donor functionalized iron(II) N-heterocyclic carbene complexes in transfer hydrogenation reactions. European Journal of Inorganic Chemistry. ISSN 1434-1948. Vol. 2021, N.º 1 (2021), pp. 22-291434-194810.1002/ejic.2020008681099-0682metadata only accessinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-08-03T10:06:16Zoai:repositorio.ipl.pt:10400.21/12744Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:20:46.582098Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
title |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
spellingShingle |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions Lopes, Rita Carbene ligands Transfer hydrogenation Reduction Ketones Microwave irradiation |
title_short |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
title_full |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
title_fullStr |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
title_full_unstemmed |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
title_sort |
Donor functionalized iron(II) N-Heterocyclic carbene complexes in transfer hydrogenation reactions |
author |
Lopes, Rita |
author_facet |
Lopes, Rita Raya-Baron, Alvaro Robalo, M. Paula S. Vinagreiro, Carolina Barroso, Sonia Romão, Maria João Fernandez, Ignacio Pereira, Mariette M. Royo |
author_role |
author |
author2 |
Raya-Baron, Alvaro Robalo, M. Paula S. Vinagreiro, Carolina Barroso, Sonia Romão, Maria João Fernandez, Ignacio Pereira, Mariette M. Royo |
author2_role |
author author author author author author author author |
dc.contributor.none.fl_str_mv |
RCIPL |
dc.contributor.author.fl_str_mv |
Lopes, Rita Raya-Baron, Alvaro Robalo, M. Paula S. Vinagreiro, Carolina Barroso, Sonia Romão, Maria João Fernandez, Ignacio Pereira, Mariette M. Royo |
dc.subject.por.fl_str_mv |
Carbene ligands Transfer hydrogenation Reduction Ketones Microwave irradiation |
topic |
Carbene ligands Transfer hydrogenation Reduction Ketones Microwave irradiation |
description |
Two piano-stool iron(II) complexes bearing N-heterocyclic carbene ligands outfitted with acetamide- and amine-pendant arms [Cp*Fe(NHC(R))(CO)I] {Cp* = eta(5)-tetramethylcyclopentadienyl; R = CH2CONEt2(3), (CH2)(2)NEt2(4)}, have been prepared and fully characterized. Their catalytic activity in transfer hydrogenation (TH) of ketones usingiPrOH as a hydrogen source and catalytic amounts of base (LiOtBu) has been explored, along with that of previously reported [CpFe(NHC(R))(CO)I] {R =nBu (5), (CH2)(2)OH (6), Et (7), and (CH2)(3)OH (8)} complexes containing hydroxyl and nonfunctionalized alkyl arms. Complex3displayed the highest catalytic activity of the whole series3-8, reaching a TOF(50)value of 533 h(-1). NMR monitoring of the stoichiometric reaction of3with LiOtBu, allowed the identification of a new species3'containing a deprotonated amidate moiety, which has been fully characterized by(1)H,C-13, and(15)N NMR. Finally, a green protocol for the reduction of ketones through TH using glycerol as a hydrogen source, under microwave irradiation in the presence of catalytic amounts of3and base has been developed. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-02-01T18:12:14Z 2021-01-08 2021-01-08T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10400.21/12744 |
url |
http://hdl.handle.net/10400.21/12744 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
LOPES, Rita; [et al] – Donor functionalized iron(II) N-heterocyclic carbene complexes in transfer hydrogenation reactions. European Journal of Inorganic Chemistry. ISSN 1434-1948. Vol. 2021, N.º 1 (2021), pp. 22-29 1434-1948 10.1002/ejic.202000868 1099-0682 |
dc.rights.driver.fl_str_mv |
metadata only access info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
metadata only access |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Wiley Online Library |
publisher.none.fl_str_mv |
Wiley Online Library |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799133477486985216 |