Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates

Madern, Nathalie; Talbi, Barisa; Salmain, Michèle

doi:10.1002/aoc.2929

Cited by 30 publications

(20 citation statements)

References 52 publications

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“…Although less prevalent throughout organometallic chemistry than HMDS, 49 amido DPA has been utilised in a number of varied branches of chemistry 50 including materials science, 51 catalysis, 52 supramolecular chemistry 53 and even in cooperative bimetallic chemistry. 54 Being the simplest of the DPA through three N sites; one central amido N and two neutral pyridyl N atoms.…”

Section: Introductionmentioning

confidence: 99%

Synthetic, structural and magnetic implications of introducing 2,2′-dipyridylamide to sodium-ferrate complexes

et al. 2017

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This version is available at https://strathprints.strath.ac.uk/60604/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Using a transamination approach to access novel Fe(II) complexes, this study presents the synthesis, X-ray crystallographic and magnetic characterisation of a series of new iron complexes containing the multifunctional 2,2-dipyridylamide (DPA) ligand using iron bis(amide) [{Fe(HMDS)2}2] and sodium ferrate [{NaFe(HMDS)3} ] (1) as precursors (HMDS = 1,1,1,3,3,3hexamethyldisilazide). Reactions of DPA(H) with 1 show exceptionally good stoichiometric control, allowing access to heteroleptic [(THF)2·NaFe(DPA)(HMDS)2] (3) and homoleptic [{THF·NaFe(DPA)3} ] (4) by using 1 and 3 equivalents of DPA(H) respectively. Linking this methodology and co-complexation, which is a more widely used approach to prepare heterobimetallic complexes, 3 can also be prepared by combining NaHMDS with heteroleptic [{Fe(DPA)(HMDS)}2] (2). In turn, 2 has been also synthesised and structurally defined by reacting [{Fe(HMDS)2}2] with two equivalents of DPA(H). Structural studies demonstrate the coordination flexibility of the N-bridged bis(heterocycle) ligand DPA, with 2 and 3 exhibiting discrete monomeric motifs, whereas 4 displays a much more intricate supramolecular structure, with one of its DPA ligands coordinating in an anti/anti fashion (as opposed to 2 and 3 where DPA shows a syn/syn conformation), which facilitates propagation of the structure via its central amido N. Magnetic studies confirmed the high-spin electron configuration of the iron(II) centres in all three compounds and revealed the existence of weak ferromagnetic interactions in dinuclear compound 2 (J = 1.01 cm -1 ). Journal Name ARTICLE

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Section: Introductionmentioning

confidence: 99%

Synthetic, structural and magnetic implications of introducing 2,2′-dipyridylamide to sodium-ferrate complexes

et al. 2017

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“…The complexes were synthesized using the dinuclear dichloro complex [{(η 5 ‐C 5 Me 5 )M(μ‐Cl)Cl} 2 ] and ligand (L 1–3 ) as per reported procedure (Scheme ) …”

Section: Methodsmentioning

confidence: 99%

Spectroscopic and electrochemical study for evaluating DNA interaction activity of 4‐(3‐halophenyl)‐6‐(pyridin‐2‐yl)pyrimidin‐2‐amine based piano stool Cp* Rh (III) and Ir (III) complexes

Vekariya

Karia

Bhatt

et al. 2019

Applied Organom Chemis

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Six novel organometallic half sandwich complexes [(η5‐C5Me5)M(L1–3)Cl]Cl.2H2O were synthesized using [{(η5‐C5Me5)M(μ‐Cl)Cl2], where M = Ir (III)/Rh (III) and L1–3 = three pyridyl pyrimidine based ligands; and characterized by NMR, Infra‐red spectroscopy, conductance, elemental and thermal analysis. The complex‐DNA binding mode and/or strength evaluated using absorption titration, electrochemical studies and hydrodynamic measurement proposed intercalative binding mode, which was also confirmed by molecular docking study. Differential pulse voltammetry and cyclic voltammetry studies indicated an alteration in oxidation and reduction potentials of complexes (M+4/M+3) in presence of CT‐DNA. The metal complexes can cleave plasmid DNA as proposed in gel electrophoretic analysis. The LC50 values of complexes evaluated on brine shrimp suggested their potent cytotoxic nature.

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“…4). First, this substrate may be readily reduced into the corresponding α-(trifluoromethyl)benzyl alcohol S9 thanks to the electron-attracting character of the CF 3 substituent [26]. Second, TFAC is well known to be hydrogenated into asymmetric trifluoromethyl benzyl alcohol by naturally occurring hydrogenases like carbonyl reductase [27], which makes it a perfect candidate for studying the enantioselectivity of the catalysis.…”

Section: Aqueous Transfer Hydrogenation Of Tfac By Metal Complexesmentioning

confidence: 99%

Artificial iron hydrogenase made by covalent grafting of Knölker's complex into xylanase: Application in asymmetric hydrogenation of an aryl ketone in water

Kariyawasam

Ghattas

Santos

et al. 2020

Biotech and App Biochem

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We report a new artificial hydrogenase made by covalent anchoring of the iron Knölker's complex to a xylanase S212C variant. This artificial metalloenzyme was found to be able to catalyze efficiently the transfer hydrogenation of the benchmark substrate trifluoroacetophenone by sodium formate in water, yielding the corresponding secondary alcohol as a racemic. The reaction proceeded more than threefold faster with the XlnS212CK biohybrid than with the Knölker's complex alone. In addition, efficient conversion of trifluoroacetophenone to its corresponding alcohol was reached within 60 H with XlnS212CK, whereas a ≈2.5‐fold lower conversion was observed with Knölker's complex alone as catalyst. Moreover, the data were rationalized with a computational strategy suggesting the key factors of the selectivity. These results suggested that the Knölker's complex was most likely flexible and could experience free rotational reorientation within the active‐site pocket of Xln A, allowing it to access the subsite pocket populated by trifluoroacetophenone.

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Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates

Cited by 30 publications

References 52 publications

Synthetic, structural and magnetic implications of introducing 2,2′-dipyridylamide to sodium-ferrate complexes

Synthetic, structural and magnetic implications of introducing 2,2′-dipyridylamide to sodium-ferrate complexes

Spectroscopic and electrochemical study for evaluating DNA interaction activity of 4‐(3‐halophenyl)‐6‐(pyridin‐2‐yl)pyrimidin‐2‐amine based piano stool Cp* Rh (III) and Ir (III) complexes

Artificial iron hydrogenase made by covalent grafting of Knölker's complex into xylanase: Application in asymmetric hydrogenation of an aryl ketone in water

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