Biomimetic Oxidation of Hydrocarbons with Air over Metalloporphyrins

Jiang, Guo‐Fang; Liu, Qiang; Guo, Can‐Cheng

doi:10.5772/13821

Cited by 4 publications

(2 citation statements)

References 104 publications

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“…Since then, the synthesis and study of these very robust macrocycles inspired by biological systems, have been incorporated into the development of sophisticated bulky, chiral, and surface linked catalysts, because of a variety of properties that turn them useful for organic synthesis (Scheme 1) [18]. and biological functions of iron porphyrin complexes were well established [15].…”

Section: General Concepts In Porphyrin Catalysismentioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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Catalysis is a topic of continuous interest since it was discovered in chemistry centuries ago. Aiming at the advance of reactions for efficient processes, a number of approaches have been developed over the last 180 years, and more recently, porphyrins occupy an important role in this field. Porphyrins and metalloporphyrins are fascinating compounds which are involved in a number of synthetic transformations of great interest for industry and academy. The aim of this review is to cover the most recent progress in reactions catalysed by porphyrins in scalable procedures, thus presenting the state of the art in reactions of epoxidation, sulfoxidation, oxidation of alcohols to carbonyl compounds and C-H functionalization. In addition, the use of porphyrins as photocatalysts in continuous flow processes is covered.

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Section: General Concepts In Porphyrin Catalysismentioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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“…All of these distinct structural features of the tetrapyrrolic macrocycles have led to a better understanding and the development of more robust catalysts based on porphyrins, enabling their use as a sophisticated bulky, chiral, and surface-linked catalysts [13].…”

Section: Introductionmentioning

confidence: 99%

Studies of the Catalytic Activity of Iron (III) Porphyrins for the Protection of Carbonyl Groups in Homogeneous Media

2019

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The protection of carbonyl groups that produce acetal products is a key reaction in fine chemistry due to the high reactivity of aldehydes and ketones in certain media. This process can be catalyzed by protic or Lewis acids. Since metalloporphyrins often possess free axial positions in the central metal, they can be applied as Lewis acid catalysts, allowing the additional coordination of substrates. Therefore, three ferric complexes were selected to be evaluated as catalysts for the acetalization of benzaldehyde with ethanol and triethyl orthoformate (TEOF) in the homogeneous phase: (i) 5,10,15,20-tetrakis(phenylporphyrin) iron (III) chloride (Fe0F); (ii) 5,10,15,20-tetrakis(2,6-difluorphenylporphyrin) iron (III) chloride (Fe2F); and (iii) 5,10,15,20-tetrakis(pentafluorphenylporphyrin) iron (III) chloride (Fe5F). The complex Fe5F showed the highest catalytic activity, and kinetic parameters were evaluated for this reaction, exhibiting an increasing rate of reaction of about 550-fold in comparison with the non-catalyzed reaction. The reaction scope was also investigated, and Fe5F was found to be active for the acetalization of benzaldehyde and acetophenone, with different protective agents such as alcohols, glycols, glycerol, and epoxide being selective for the formation of cyclic acetals. The protection of benzaldehyde with ethylene glycol and propylene glycol were also studied at different temperatures, and turnover frequency (TOF) values of up to 360 h−1 were determined at 40 °C in homogenous media without the need for solvent or drying agents.

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Theoretical studies and industrial applications of oxidative activation of inert C-H bond by metalloporphyrin-based biomimetic catalysis

Liu

Guo

2012

Sci. China Chem.

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Biomimetic Oxidation of Hydrocarbons with Air over Metalloporphyrins

Cited by 4 publications

References 104 publications

Porphyrins as Catalysts in Scalable Organic Reactions

Porphyrins as Catalysts in Scalable Organic Reactions

Studies of the Catalytic Activity of Iron (III) Porphyrins for the Protection of Carbonyl Groups in Homogeneous Media

Theoretical studies and industrial applications of oxidative activation of inert C-H bond by metalloporphyrin-based biomimetic catalysis

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