Effect of N-based additive on the optimization of liquid phase oxidation of bicyclic, cyclic and aromatic alcohols catalyzed by dioxidomolybdenum(<scp>vi</scp>) and oxidoperoxidomolybdenum(<scp>vi</scp>) complexes

Maurya, Mannar R.; Saini, Neeraj; Avecilla, Fernando

doi:10.1039/c5ra16490g

Cited by 16 publications

(13 citation statements)

References 42 publications

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“…[18b], , This is in agreement with the hypothesis that electron‐withdrawing substituents on the hydrazone ligands might affect the formation of such species and consequently the overall catalytic activity. In comparison with the previously reported activities for the catalytic oxidation of olefins and sulfides by Mo VI complexes,, the catalytic activities of the complexes reported in this study are in the normal range.…”

Section: Resultssupporting

confidence: 87%

“…Although the details of catalytic mechanism were not studied in the present work, on the basis of previous studies on similar systems, and the electronic absorption spectrum of 2 (see the Supporting Information, Figure S8), it is predicted that the key step in this catalytic process is the oxidation of the substrate by an oxidoperoxidomolybdenum–hydrazone species. The electronic absorption spectrum indicates that the solution of 2 in methanol is sensitive to the addition of H 2 O 2 .…”

Section: Resultsmentioning

confidence: 95%

“…Among the metal‐based catalysts, Mo‐containing compounds are highly active catalysts for oxidation reactions in the presence of peroxides, and some of them are currently used in several industrial processes. Oxidomolybdenum(VI) complexes synthesized from the reactions of molybdenum(VI) ions and organic ligands are one of the most efficient classes of (pre)catalysts for oxidation reactions that have been investigated during recent decades . Interestingly, such complexes have structural similarities with a class of mononuclear molybdoenzymes capable of transferring oxygen atoms and can be used as suitable models to mimic biological systems .…”

Section: Introductionmentioning

confidence: 99%

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Electronic Effects of Aromatic Rings on the Catalytic Activity of Dioxidomolybdenum(VI)–Hydrazone Complexes

et al. 2017

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A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription. This manuscript has been accepted after peer review and appears as an Accepted Article online prior to editing, proofing, and formal publication of the final Version of Record (VoR). This work is currently citable by using the Digital Object Identifier (DOI) given below. The VoR will be published online in Early View as soon as possible and may be different to this Accepted Article as a result of editing. Readers should obtain the VoR from the journal website shown below when it is published to ensure accuracy of information. The authors are responsible for the content of this Accepted Article. FULL PAPER Electronic effects of aromatic rings on the catalytic activity of dioxidomolybdenum(VI)-hydrazone complexesRahman Bikas, [a,*] Vito Lippolis, [b,*] Nader Noshiranzadeh, [a] Hossein Farzaneh-Bonab, [a] Alexander J. Blake, [c] Milosz Siczek, [d] Hassan Hosseini-Monfared, [a] and Tadeusz Lis [d] Abstract:Nine dioxidomolybdenum(VI) complexes were synthesized by the reaction of MoO3 with tridentate hydrazone Schiff base ligands obtained from the reaction of aromatic acid hydrazides (3-hydroxy-2-naphthoic acid hydrazide, 4-pyridine carboxylic acid hydrazide or 2-furane carboxylic acid hydrazide) and ortho-hydroxy aldehyde derivatives (5-iodo-2-hydroxybenzaldehyde, 2-hydroxy-1-naphthaldehyde or 2-hydroxy-3-methoxybenzaldehyde). All ligands and complexes were characterized by elemental analysis and spectroscopic methods. The structures of seven complexes were further elucidated by single-crystal X-ray diffraction analysis which indicated a distorted octahedral geometry at the metal centre. Spectroscopic and X-ray analyses indicated that the ligands are coordinated to the molybdenum(VI) ion as dinegative ligands due to deprotonation of phenolic OH and amidic NH groups upon complexation. These complexes were used as catalyst in the oxidation of cyclooctene and thioanisole in the presence of hydrogen peroxide as environmental friendly oxidant. In order to achieve the highest catalytic activity, the effects of important parameters such as solvent, temperature and the molar ratio of oxidant to substrate were optimized. The results indicate that electron-withdrawing substituents on the ligands increase the catalytic activity of dioxidomolybdenum(VI)-hydrazone complexes.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

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Electronic Effects of Aromatic Rings on the Catalytic Activity of Dioxidomolybdenum(VI)–Hydrazone Complexes

et al. 2017

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“…(Ep)oxidation of alkenes and alcohols catalyzed by Mo (VI)‐complexes was intensively studied in recent years . Mo VI O 2 ‐complexes are routinely used in the production of industrial propylene oxide and in the efficient chemoselective oxidation of linear and branched alkenes . Recently, the molybdenum (VI) complex of picolinic acid‐based metallomicellar catalyst was used in the controlled and chemoselective oxidation of the activated alcohols in the aqueous medium, which afforded high sufficiency .…”

Section: Introductionmentioning

confidence: 99%

Bis‐dioxomolybdenum (VI) oxalyldihydrazone complexes: Synthesis, characterization, DFT studies, catalytic epoxidation potential, molecular modeling and biological evaluations

Adam

Ahmed

Elhady

et al. 2020

Applied Organom Chemis

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Two cis‐bis‐dioxomolybdenum oxalylsalicylidenedihydrazone complexes (MoO2L1 and MoO2L2) were synthesized via the complexation of dioxomolybdenum (VI) acetylacetonate with oxalylsalicylidenedihydrazone (H2L1) and p‐sodium sulfonate oxalylsalicylidenedihydrazone (H2L2) bis‐Schiff base chelating ligands, respectively. The structures of the newly synthesized complexes were confirmed by 1H‐ and 13C‐NMR, IR, ultraviolet–visible and mass spectra, as well as elemental analyses (EA) and conductivity measurements. The spectrophotometric continuous variation method revealed the formation of 2: 1 (metal: ligand molar ratios). DFT studies were applied for the ligands and their Mo‐chelates. Interestingly, the bis‐MoO2(VI) oxalyldihydrazone complexes showed remarkable catalytic sufficiency towards the selective (ep)oxidation of 1,2‐cyclooctene, benzyl alcohol and thiophene using H2O2 or tert‐butyl hydroperoxide (tBuOOH) at 85 °C. Under aqueous conditions, the MoO2L2 (with p‐sodium sulfonate substituent) exhibited superior that of the MoO2L1 (without p‐NaSO3―group), highlighting the role of sodium sulfonate substituent in the catalytic progress of the Mo‐chelate. The ligands (H2L1 and H2L2) and their corresponding Mo‐complexes (MoO2L1 and MoO2L2) were assessed for their antitumor and antimicrobial activities. Furthermore, the antioxidant activity was also evaluated using the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and superoxide dismutase (SOD) assays. The binding nature between the Mo‐complexes and calf thymus DNA (ctDNA) was also studied within spectroscopic and hydrodynamic techniques.

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“…Many 3 d transition metals (V, Mo, Fe, Cu) are attractive in terms of their abundance and low cost as the active centres for aerobic oxidation processes. [3d], In particular, vanadium complexes are well known as an attractive class of catalysts,, mediating the aerobic oxidation of organic substrates including benzylic, allylic, and propargylic alcohols . Hanson and co‐workers have shown that the complex (HQ) 2 VO(O i Pr) (HQ = 8‐quinolinate) ( I , Figure ) efficiently catalyzed the oxidation of benzylic, allylic, and propargylic alcohols with air in the presence of NEt 3 .…”

Section: Introductionmentioning

confidence: 99%

Vanadium Aminophenolate Complexes and Their Catalytic Activity in Aerobic and H2O2‐Mediated Oxidation Reactions

2016

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Effect of N-based additive on the optimization of liquid phase oxidation of bicyclic, cyclic and aromatic alcohols catalyzed by dioxidomolybdenum(vi) and oxidoperoxidomolybdenum(vi) complexes

Abstract: Catalytic potentials of [MoVIO2]2+ and [MoVIO(O2)]2+ complexes with dibasic tridentate ONO donor ligands for the oxidation of bicyclic, cyclic and aromatic alcohols in the presence of NEt3 are reported.

Cited by 16 publications

References 42 publications

Electronic Effects of Aromatic Rings on the Catalytic Activity of Dioxidomolybdenum(VI)–Hydrazone Complexes

Electronic Effects of Aromatic Rings on the Catalytic Activity of Dioxidomolybdenum(VI)–Hydrazone Complexes

Bis‐dioxomolybdenum (VI) oxalyldihydrazone complexes: Synthesis, characterization, DFT studies, catalytic epoxidation potential, molecular modeling and biological evaluations

Vanadium Aminophenolate Complexes and Their Catalytic Activity in Aerobic and H2O2‐Mediated Oxidation Reactions

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