Asymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones and o-Hydroxyphenyl Ketones Using Noyori-Ikariya Catalysts

Página do item simplificado
dc.creatorYe Zheng
dc.creatorJaime A. Martinez-Acosta
dc.creatorMohammed Khimji
dc.creatorLuiz Cláudio de Almeida Barbosa
dc.creatorGuy J. Clarkson
dc.creatorMartin Wills
dc.date.accessioned2023-11-17T20:53:12Z
dc.date.accessioned2025-09-09T00:36:56Z
dc.date.available2023-11-17T20:53:12Z
dc.date.issued2022-11-14
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.3390/ecsoc-25-11774
dc.identifier.issn2673-4583
dc.identifier.urihttps://hdl.handle.net/1843/61104
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofChemistry Proceedings
dc.rightsAcesso Aberto
dc.subjectQuímica
dc.subjectCatálise
dc.subjectRedução (Química)
dc.subjectHidrogenação
dc.subject.otherCatalysis
dc.subject.otherNoyori catalyst
dc.subject.otherReduction
dc.subject.otherEnatioselective reduction
dc.titleAsymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones and o-Hydroxyphenyl Ketones Using Noyori-Ikariya Catalysts
dc.typeArtigo de periódico
local.citation.epage11
local.citation.issue1
local.citation.spagee35
local.citation.volume8
local.description.resumoIn 1995, Noyori and co-workers made a breakthrough with their design of practical ruthenium-based catalysts, which combined the homochiral TsDPEN ligand with a Ru(II) arene [1,2]. Using (R,R)-1 at a loading of 0.5 mol% in either KOH-iPrOH or the azeotropic mixture of formic acid–triethylamine (FA:TEA, 5:2 molar ratio), the reduction of acetophenone was achieved in up to 98% ee (Figure 1).The mechanism for the asymmetric transfer hydrogenation (ATH) with Noyori–Ikariya catalysts is now well-established (Figure 2) [3,4,5,6,7,8,9]. The precatalyst can be activated by elimination of HCl to form a 16-electron neutral Ru(II) complex. Then, the 16-electron complex abstracts two hydrogen atoms from the hydrogen donor, such as isopropanol, a formic acid/triethylamine (FA/TEA) mixture or sodium formate, to form a hydride that contains an 18-electron Ru(II) centre. Finally, the two hydrogen atoms are transferred to the C=O group and reduce ketone substrates into chiral alcohol products. Meanwhile, the 16-electron neutral Ru(II) complex is regenerated and can restart the catalytic cycle. The six-membered transition state can be stabilized by the combination of electrostatic interactions and steric effects. Edge/face (or CH/π) electrostatic interaction makes the electron-rich aryl group of a substrate favour the position adjacent to the η6-arene ring of the catalyst (Figure 3), whereas the large group and electron group favour the position distal to η6-arene ring (Figure 4).
local.identifier.orcidhttps://orcid.org/0000-0001-9620-7302
local.identifier.orcidhttps://orcid.org/0000-0002-5395-9608
local.publisher.countryBrasil
local.publisher.departmentICEX - INSTITUTO DE CIÊNCIAS EXATAS
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttp://https://doi.org/10.3390/ecsoc-25-11774

Arquivos

Pacote original

Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
Asymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones and o-Hydroxyphenyl Ketones Using Noyori-Ikariya Catalysts.pdf
Tamanho:
1.55 MB
Formato:
Adobe Portable Document Format
Baixar

Licença do pacote

Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
License.txt
Tamanho:
1.99 KB
Formato:
Plain Text
Descrição:
Baixar

Coleções

Artigo de Periódico

Logo UFMG