Catalytic oxidation of a model volatile organic compound (toluene) with tetranuclear Cu(II) complexes

Sutradhar, Manas; Alegria, Elisabete C. B. A.; Barman, Tannistha Roy; Lapa, Hugo M.; Silva, M. Fátima C. Guedes da; Pombeiro, Armando J. L.

doi:10.1016/j.ica.2021.120314

Cited by 12 publications

(9 citation statements)

References 57 publications

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“…Both the complexes catalyzed the side-chain oxidation to produce benzaldehyde and benzyl alcohol as the major and minor products, respectively. While comparing the activity of tautomers 100 and 101 , the latter was found to be the most active one, with an overall product yield of 38.7% and benzaldehyde selectivity of 98.5% …”

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

“…For instance, a substantial decrease in the product yield upon adding radical traps such as CBrCl 3 , TEMPO, and diphenylamine indicated a radical-mediated mechanism for the oxidation. The possible catalytic mechanism for the oxidation reaction is provided in Figure . ,,, Primarily, a metal-assisted formation of oxygen-based radicals ( t- BuOO • / t- BuO • or HOO • /HO • ) occurs via the interaction of oxidant with the metal center. In the next step, the formed t- BuO • or HO • abstracts one hydrogen atom from toluene (RH) to form R • , and its subsequent interaction with Cu II –OOH results in the formation of alkyl hydroperoxide.…”

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

“…174 Later, a series of tautomeric Cu(II) complexes 100−103 (Figure 28) were employed for the oxidation of toluene using tert-butyl hydroperoxide or H 2 O 2 (Table 10). 175,176 Even though all the complexes catalyzed sidechain oxidation, the tautomeric complexes 102 and 103 resulted in the formation of ring oxidized products as well. With catalyst 102, the selectivity toward benzaldehyde was higher at low catalyst loading, and it switched to o-cresol at high catalyst loading.…”

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

“…While comparing the activity of tautomers 100 and 101, the latter was found to be the most active one, with an overall product yield of 38.7% and benzaldehyde selectivity of 98.5%. 176 In general, toluene is a simple yet useful substrate for predicting the mechanism of aromatic oxidation. As toluene is unfunctionalized, there is no possibility for toluene coordination with the metal center to affect the catalytic activity and selectivity.…”

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

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Rational Design of First-Row Transition Metal Complexes as the Catalysts for Oxidation of Arenes: A Homogeneous Approach

2022

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Researchers have always been intrigued by one-step selective hydroxylation of aromatic compounds since achieving adequate selectivity toward the target product and avoiding overoxidation are challenging. However, the naturally available oxygenase enzymes efficiently and selectively perform such transformations under normal atmospheric conditions. Inspired by naturally occurring oxygenase enzymes, researchers have undertaken numerous attempts to catalyze the oxidation of arenes using homogeneous and heterogeneous catalysts. In this regard, the first-row transition metal complexes are considered as candidates due to their abundance and redox characteristics. Therefore, this review focuses on catalyst design strategies to improve the efficiency and selectivity of arene oxidation and illustrates the distinctive homogeneous approaches reported in this area by employing first-row transition metal complexes.

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Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

Section: Aromatic Versus Aliphatic Oxidations In Alkylbenzenesmentioning

confidence: 99%

See 2 more Smart Citations

Rational Design of First-Row Transition Metal Complexes as the Catalysts for Oxidation of Arenes: A Homogeneous Approach

2022

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“…Significant progress has been made in the field of homogeneous catalytic oxidation of toluene using various abundant first-row transition metal catalysts that show promising catalytic activities. − Manganese-based catalysts have gained considerable attention due to the high natural abundance and varied oxidation states (−3 to +7) of this metal. ,− Although hydrocarbon catalytic oxidation reactions based on Mn complexes have been intensively studied, − their utilization for homogeneous oxidation of toluene is still very scarce …”

Section: Introductionmentioning

confidence: 99%

Cagelike Manganesesilsesquioxane Complexes: Synthesis via an Acetone Approach, Structure, and Catalytic Activity for Toluene Oxidation

Bilyachenko,

Gutsul,

Khrustalev

et al. 2023

Crystal Growth & Design

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The study describes a new feature in the self-assembly of cagelike manganese-based phenylsilsesquioxanes consisting of the strong influence of acetone solvates on the formation of a cage structure. By this convenient approach, a series of new tri and tetra manganese-based silsesquioxane complexes with (i) 1,10-phenanthroline, (ii) pyrazine, or (iii) 3,5-dimethylpyrazole (dmpzH) ligands were isolated and characterized. Single-crystal X-ray diffraction studies established the molecular architectures of all of the synthesized products. Several compounds represent extraordinary types of cagelike metallasilsesquioxane (CLMS) molecular architectures. Pyrazine- and dmpzH-based Mn3Na3 compounds exhibit total oxidation of initial Mn(II) ions to the Mn(III) state. They present relatively weak antiferromagnetic interactions between the manganese centers. The catalytic performance of a representative precatalyst Mn–CLMS compound, [(Ph6Si6O12)2Mn3Na3(dmpzH)3(acetone)3(H2O)], was investigated for the microwave-assisted oxidation of toluene to obtain benzaldehyde, benzyl alcohol, and benzoic acid as the main products. The effects of reaction parameters were studied, and under optimized conditions, using the t BuOOH oxidant, the oxygenated products were formed with a total yield of 54%, under microwave irradiation at 100 °C after 6 h, with 70% selectivity toward the formation of benzoic acid.

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Catalytic Oxidation ofVOCs to Value‐added Compounds Under Mild Conditions

Alegria,

Sutradhar,

Barman

2024

Catalysis for a Sustainable Environment

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Catalytic oxidation of a model volatile organic compound (toluene) with tetranuclear Cu(II) complexes

Cited by 12 publications

References 57 publications

Rational Design of First-Row Transition Metal Complexes as the Catalysts for Oxidation of Arenes: A Homogeneous Approach

Rational Design of First-Row Transition Metal Complexes as the Catalysts for Oxidation of Arenes: A Homogeneous Approach

Cagelike Manganesesilsesquioxane Complexes: Synthesis via an Acetone Approach, Structure, and Catalytic Activity for Toluene Oxidation

Catalytic Oxidation ofVOCs to Value‐added Compounds Under Mild Conditions

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