Ruthenium(II) carbonyl complexes designed with arsine and PNO/PNS ligands as catalysts for N-alkylation of amines via hydrogen autotransfer process

Ramachandran, R.; Prakash, Govindan; Nirmala, Muthukumaran; Viswanathamurthi, Periasamy; Małecki, Jan Grzegorz

doi:10.1016/j.jorganchem.2015.05.054

Cited by 43 publications

(18 citation statements)

References 108 publications

(23 reference statements)

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“…benzazoles, benzoxazoles, or benzothiazoles. In a subsequent report, comparable catalytic activity was demonstrated for complexes of the type [RuCl(CO)(AsPh 3 )(L)] (41) where L = 2-(2-(diphenylphosphino)benzylidene)-N-ethyl-thiosemi carbazone or 2-(2-(diphenylphosphino) benzylidene)-N-cyclohexyl-thiosemicarbazone ( Figure 7) [143]. The authors propose that the mechanism for the reaction is via a so-called "borrowed hydrogen" pathway, whereby the alcohol is catalytically dehydrogenated to the corresponding aldehyde, which then condenses with the amine to give an intermediate imine, which is subsequently hydrogenated by the catalyst.…”

Section: Carbon-heteroatom Coupling Reactionsmentioning

confidence: 74%

“…The conditions used involved a catalyst loading of 0.1 mol%, KOH as base, toluene as solvent and heating to 100 • C for 12 h. Good to excellent yields, TONs of up to 990 and TOFs of up to 83 h -1 were obtained, in particular for complex in which R is the CH 3 group. Several reports have also appeared from the group of Viswanathamurthi and co-workers concerning C-N coupling reactions catalysed by ruthenium complexes [74,[142][143][144][145]. The initial report briefly describes the benzylation of aniline catalysed by ruthenium hydroxyquinolinethiosemicarbazone complexes 39 ( Figure 7) at 100 °C under nitrogen in the presence of KOBu t .…”

Section: Carbon-heteroatom Coupling Reactionsmentioning

confidence: 99%

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Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

Kostas

Steele

2020

Catalysts

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Catalysis of cross-coupling reactions under phosphane-free conditions represents an important ongoing challenge. Although transition metal complexes based on the thiosemicarbazone unit have been known for a very long time, their use in homogeneous catalysis has been studied only relatively recently. In particular, reports of cross-coupling catalytic reactions with such complexes have appeared only in the last 15 years. This review provides a survey of the research in this area and a discussion of the prospects for future developments.

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Section: Carbon-heteroatom Coupling Reactionsmentioning

confidence: 74%

Section: Carbon-heteroatom Coupling Reactionsmentioning

confidence: 99%

Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

Kostas

Steele

2020

Catalysts

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“…A possible catalytic cycle is proposed in Scheme on the basis of the results obtained and available literature on similar ruthenium catalyzed transformations . This catalysis is considered toproceed via the (benzyloxy) ruthenium intermediate A , which undergoes b‐hydrogen elimination to give the ruthenium hydride B .…”

Section: Resultsmentioning

confidence: 99%

Novel N‐Alkylbenzimidazole‐Ruthenium (II) complexes: Synthesis and catalytic activity of N‐alkylating reaction under solvent‐free medium

Şahin

Özdemir

Gürbüz

et al. 2018

Applied Organom Chemis

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In this article, direct N‐alkylation reactions of amines with alcohols derivatives have been investigated. For this purpose, a new series ruthenium (II) complexes bearing N‐coordinated benzimidazole complexes with have been synthesized and fully characterized by elemental analysis, FT‐IR, 1H NMR and, 13C NMR spectroscopies. Additionally, the structures of the complexes 2b and 2c have been confirmed by X‐ray crystallography. Although the N‐alkylating reaction is usually performed in toluene, the catalytic study of complexes 2a‐d has carried out no additional solvent and alcohol acted both as solvent and reactant of alkylating by using a little excess of alcohols. Surprisingly, conversion and selectivity of amine product for alkylation reaction have been seen high in medium solvent‐free relative to in toluene.

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“…Yarı-sandviç Ru(II)-aren kompleksleri, alkilasyon, aminasyon, hidrojenasyon, hidroformilasyon ve izomerizasyon reaksiyonlarında katalizör olarak kullanılmaktadır [9][10][11]. Bu bileşiklerin homojen kataliz ve organik sentez alanlarında da önemli uygulamaları vardır [12][13][14].…”

Section: Introductionunclassified

Ruthenium(II) half-sandwich complexes containing N-substituted 5-nitrobenzimidazole: Synthesis, structures and catalytic transfer hydrogenation of ketones

Buldurun¹,

Özdemır²

2019

Düzce Üniversitesi Bilim Ve Teknoloji Dergisi

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ÖZET Bu çalışmada N-koordineli 5-nitrobenzimidazol ligandlarının [RuCl 2 (p-simen)] 2 metal tuzu ile reaksiyonlarında yeni altı kompleks bileşik hazırlandı ve yapıları, elemental analiz, IR ve 1 H-13 C NMR spektroskopik tekniklerle aydınlatıldı. Sentezlenen Ru(II) kompleksleri, transfer hidrojenasyonu için katalizör olarak test edildi. Kompleksler, 80 °C"de KOH varlığında, çeşitli sübstitüe ketonların hidrojen transfer tepkimelerindeki katalitik aktiviteleri incelendi ve %100"e kadar bir dönüşüm gösterdi. Komplekslerin aktif katalizörler olduğu bulundu. ABSTRACTIn this study, N-substituted 5-nitrobenzimidazole ligands were reacted with [RuCl 2 (p-cymene)] 2 and the corresponding a new six complex compound were prepared and their structure were elucidated by elemental analysis, IR and 1 H-13 C NMR spectroscopic techniques. The synthesized Ru(II) complexes were tested as catalysts for the transfer hydrogenation. The complexes were examined for their efficiency as a catalyst in the transfer hydrogenation of varied of substituted ketones to alcohols in the presence of KOH, at 80 °C and exhibited a finest conversion up to %100. The complexes find out the active catalysts.

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Ruthenium(II) carbonyl complexes designed with arsine and PNO/PNS ligands as catalysts for N-alkylation of amines via hydrogen autotransfer process

Cited by 43 publications

References 108 publications

Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

Novel N‐Alkylbenzimidazole‐Ruthenium (II) complexes: Synthesis and catalytic activity of N‐alkylating reaction under solvent‐free medium

Ruthenium(II) half-sandwich complexes containing N-substituted 5-nitrobenzimidazole: Synthesis, structures and catalytic transfer hydrogenation of ketones

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