Ruthenium Porphyrin‐Catalyzed Aerobic Oxidation of Terminal Aryl Alkenes to Aldehydes by a Tandem Epoxidation–Isomerization Pathway

Jiang, Gaoxi; Chen, Jian; Thu, Hung‐Yat; Huang, Jie‐Sheng; Zhu, Nanqun; Che, Chi‐Ming

doi:10.1002/ange.200801500

Cited by 19 publications

(4 citation statements)

References 52 publications

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“…Che et al. developed a good alternative method to the Wacker oxidation for converting alkenes to aldehydes directly by using the ruthenium porphyrin catalyst 55 (Figure ) whereby the epoxide was an intermediate . The salient feature of this reaction was that oxygen from the air was used for the oxidation and hence it is an open‐to‐air reaction which is an improvement over the method reported by the same group earlier by using 2,6‐dichloropyridine N ‐oxide as the oxidizing agent …”

Section: Epoxides To Carbonyl Compoundsmentioning

confidence: 99%

Isomerization of Epoxides

Jat

Kumar

2019

Adv Synth Catal

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Epoxides are highly useful synthetic intermediates andt hey can be synthesized stereo-andr egioselectively.D ue to the strained three-membered ring, their synthetic utility is limited. In many cases, it would be better to transform epoxides to other stable functional groups which could be used further in the synthesis. This isomerization would offer an alternate pathway to utilize the synthetic potential of epoxides.D espite the potential of such isomerization reactions,t hey have not been widely explored by chemists.Inthis review,the methods to isomerize epoxides into stablef unctional groups such as alcohols, aldehydes, ketones as well as trans-epoxides,b oth stereo-and regioselectively,are discussed.1I ntroduction 2E poxides to Alcohols 3E poxides to Carbonyl Compounds 4E poxy Alochols to Carbonyl Compounds by the Semipinacol Rearrangement 5 cis-trans IsomerizationofE poxides 6C onclusion

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Section: Epoxides To Carbonyl Compoundsmentioning

confidence: 99%

Isomerization of Epoxides

Jat

Kumar

2019

Adv Synth Catal

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“…In the case of terminal aliphatic olefins, the reactions required 80 °C when using a mixture of DCE (1,2‐dichloroethane) and dioxane as the solvents. Such high anti‐Markovnikov selectivity was rationalized by the formation of a transient epoxide that undergoes in situ isomerization similar to that known for ruthenium(IV) porphyrin catalysts [13b,c] …”

Section: Iron‐based Catalysts For Wacker‐type Reactionsmentioning

confidence: 88%

Sustainable Wacker‐Type Oxidations

et al. 2022

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The Wacker reaction is the oxidation of olefins to ketones and typically requires expensive and scarce palladium catalysts in the presence of an additional copper co-catalyst under harsh conditions (acidic media, high pressure of air/dioxygen, elevated temperatures). Such a transformation is relevant for industry, as shown by the synthesis of acetaldehyde from ethylene as well as for fine-chemicals, because of the versatility of a carbonyl group placed at specific positions. In this regard, many contributions have focused on controlling the chemo-and regioselectivity of the olefin oxidation by means of well-defined palladium catalysts under different sets of reaction conditions. However, the development of Wacker-type processes that avoid the use of palladium catalysts has just emerged in the last few years, thereby paving the way for the generation of more sustainable procedures, including milder reaction conditions and green chemistry technologies. In this Minireview, we discuss the development of new catalytic processes that utilize more benign catalysts and sustainable reaction conditions.

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“…Organic metal complexes, one kind of homogeneous catalytic system being widely studied, have attracted much more attention for the flexible alteration of the active metal sites and organic ligands 2. Complexation between these two parts plays an important role during the catalytic process, and the catalytic ability of active metal center could be obviously improved with the proper choice of organic ligand 2c,d…”

Section: Methodsmentioning

confidence: 99%

A Complexation Promoted Organic N‐Hydroxy Catalytic System for Selective Oxidation of Toluene

Zhang

Chen

et al. 2011

Adv Synth Catal

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Complexation was innovatively utilized to design a novel catalytic system for the selective oxidation of toluene, which runs contrary to the traditional definition of organic metal complex catalysis. In the present system, an N-heteroaromatic ringcontaining N-hydroxy compound acts as the catalytically active component. Through an electron-withdrawing effect produced by the occurring complexation with proper metal salts, which was characterized by real-time in situ Fourier transform infrared spectra, the activity of the organic molecule could be remarkably improved. The combination of copper(II) chloride with 6-hydroxy-pyrroloA C H T U N G T R E N N U N G [3,4-b]pyrazine-5,7-dione showed the best activity, and an inert hydrocarbon such as toluene could be efficiently transformed with 70.9% conversion and 93.5% selectivity to benzoic acid at 90 8C within 2 h.

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Ruthenium Porphyrin‐Catalyzed Aerobic Oxidation of Terminal Aryl Alkenes to Aldehydes by a Tandem Epoxidation–Isomerization Pathway

Cited by 19 publications

References 52 publications

Isomerization of Epoxides

Isomerization of Epoxides

Sustainable Wacker‐Type Oxidations

A Complexation Promoted Organic N‐Hydroxy Catalytic System for Selective Oxidation of Toluene

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