Heterogeneous Catalytic Aqueous Phase Oxidative Cleavage of Styrenes to Benzaldehydes: An Environmentally Benign Alternative to Ozonolysis

Schäfer, Christian; Ellstrom, Clifford J.; Török, Béla

doi:10.1007/s11244-018-0961-y

Cited by 13 publications

(8 citation statements)

References 46 publications

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“…A similar effect of a radical initiator and scavenger have been observed in the KSF montmorillonite systems, for which a radical-type mechanism has been proposed. 19 When BaFeO 3−δ was removed by hot filtration after 16 h, the reaction did not stop and proceeded in a similar way to that without the filtration step (Fig. S3, ESI †).…”

Section: Catalysis Science and Technology Communicationmentioning

confidence: 88%

“…Notes and references ‡ While oxidative cleavage of styrene with O 2 has been reported for some heterogeneous iron-based catalytic systems, there are only two examples of all-inorganic heterogeneous catalysts such as KSF 19 montmorillonite and hollow Fe 3 O 4 nanoshells. 18…”

Section: Author Contributionsmentioning

confidence: 99%

“…Other Mn-, Co-, Ni-, Cu-, and Ru-containing oxides (SrMnO 3 , BaMnO 3 , activated MnO 2 , BaCoO 3 , LaCoO 3 , Co 3 O 4 , LaNiO 3 , NiO, CuO, and BaRuO 3 ) were also inactive. In the presence of commercially-available Fe 3 O 4 nanoparticles and montmorillonite K10, which have been reported to be active for the oxidative cleavage of 1a to 2a, 18,19 no formation of 2a was observed under the reaction conditions employed.…”

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confidence: 98%

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Aerobic oxidative CC bond cleavage of aromatic alkenes by a high valency iron-containing perovskite catalyst

Shibata

Kamata

Hara

2021

Catal. Sci. Technol.

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Section: Catalysis Science and Technology Communicationmentioning

confidence: 88%

Section: Author Contributionsmentioning

confidence: 99%

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confidence: 98%

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Aerobic oxidative CC bond cleavage of aromatic alkenes by a high valency iron-containing perovskite catalyst

Shibata

Kamata

Hara

2021

Catal. Sci. Technol.

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“…The activities of styrene and 1,2-disubstituted alkenes are checked under the optimized conditions (Table ). As a result, styrene was oxidized to benzaldehyde ( 2a ) with 70% conversion and in 57% yield by A-CQDs as a nonmetal catalyst, which had much better results in comparison to the previous carbocatalytic systems based on doped graphene. , Additionally, in the presence of transition metal-based catalysts like Rh/Al 2 O 3 , benzaldehyde was produced from styrene in only 45% yield, during the 27 h reaction time …”

Section: Resultsmentioning

confidence: 98%

Amphiphilic Carbon Quantum Dots as a Bridge to a Pseudohomogeneous Catalyst for Selective Oxidative Cracking of Alkenes to Aldehydes: A Nonmetallic Oxidation System

Hadian-Dehkordi

Rezaei

Ramazani

et al. 2020

ACS Appl. Mater. Interfaces

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The oxidative cleavage of alkenes to the corresponding aldehydes using new amphiphilic carbon quantum dots (A-CQDs) as a pseudohomogeneous carbocatalyst is achieved for the first time through green and sustainable chemical processes. In this work, we successfully design a recyclable pseudohomogeneous catalyst based on A-CQDs, which is decorated with 1-aminopropyl-3-methyl-imidazolium chloride and stearic acid. The functionalization is conducted to introduce a hydrophilic/hydrophobic functionality on the surface of the catalyst to achieve high catalyst availability in polar and nonpolar media with the green goal of eliminating organic (co)solvents and additives. This amphiphilic carbocatalyst provides high mass transferability to the biphasic system, which is beneficial to promoting the oxidative cracking of a variety of olefins into corresponding aldehydes with a substrate/A-CQD ratio of 150. Around 87% of the substrates are converted to the related aldehydes using the carbocatalyst in the presence of H2O2, in pure water, without using a phase-transfer catalyst or any additives and organic solvents, which is comparable with the current metal-based cleavage systems. Surprisingly, A-CQDs exhibit high catalytic activity for the scission of electron-deficient CC bond of coumarin derivatives, accompanied by the cleavage of C–O bonds to produce the corresponding salicylaldehyde derivatives without overoxidation to acid. As a brief conclusion, A-CQDs exhibit high conversion efficiency without significant loss of activity even after six catalytic cycles. The conversion of alkenes into aldehydes is fast and high-throughput without overoxidation to acids and is accompanied by excellent solubility and stability in various solvents. Moreover, the product and the catalyst are recoverable from the reaction medium by simple extraction. So, this pseudohomogeneous carbocatalyst promises new horizons in imminent “catalytic age”. All in all, this paper provides a significant and novel advancement in carbocatalyst chemistry.

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“…The solid acid KSF montmorillonite successfully catalyzed the aqueous phase oxidative cleavage of styrenes to benzaldehyde with air, in a process that can be viewed as an environmentally benign alternative to ozonolysis (Scheme 46 ) [ 132 ]. Although the reaction showed high selectivity and conversion in the oxidation of styrene, the cleavage of substituted derivatives occurred in lower yields and selectivities.…”

Section: Synthetic Applications In Heterogeneous Systemsmentioning

confidence: 99%

Organic Synthesis Using Environmentally Benign Acid Catalysis

Kokel

Schäfer

Török

2019

COS

Self Cite

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Recent advances in the application of environmentally benign acid catalysts in organic synthesis are reviewed. The work includes three main parts; (i) description of environmentally benign acid catalysts, (ii) synthesis with heterogeneous and (iii) homogeneous catalysts. The first part provides a brief overview of acid catalysts, both solid acids (metal oxides, zeolites, clays, ion-exchange resins, metal-organic framework based catalysts) and those that are soluble in green solvents (water, alcohols) and at the same time could be regenerated after reactions (metal triflates, heteropoly acids, acidic organocatalysts etc.). The synthesis sections review a broad array of the most common and practical reactions such as Friedel-Crafts and related reactions (acylation, alkylations, hydroxyalkylations, halogenations, nitrations etc.), multicomponent reactions, rearrangements and ring transformations (cyclizations, ring opening). Both the heterogeneous and homogeneous catalytic synthesis parts include an overview of asymmetric acid catalysis with chiral Lewis and Brønsted acids. Although a broad array of catalytic processes are discussed, emphasis is placed on applications with commercially available catalysts as well as those of sustainable nature; thus individual examples are critically reviewed regarding their contribution to sustainable synthesis.

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Heterogeneous Catalytic Aqueous Phase Oxidative Cleavage of Styrenes to Benzaldehydes: An Environmentally Benign Alternative to Ozonolysis

Cited by 13 publications

References 46 publications

Aerobic oxidative CC bond cleavage of aromatic alkenes by a high valency iron-containing perovskite catalyst

Aerobic oxidative CC bond cleavage of aromatic alkenes by a high valency iron-containing perovskite catalyst

Amphiphilic Carbon Quantum Dots as a Bridge to a Pseudohomogeneous Catalyst for Selective Oxidative Cracking of Alkenes to Aldehydes: A Nonmetallic Oxidation System

Organic Synthesis Using Environmentally Benign Acid Catalysis

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