Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes

Yasukawa, Naoki; Yokoyama, H.; Masuda, Masahiro; Monguchi, Yasunari; Sajiki, Hironao; Sawama, Yoshinari

doi:10.1039/c7gc03819d

Cited by 28 publications

(25 citation statements)

References 29 publications

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“…Then, an intramolecular nucleophilic substitution of the bromide by enolate takes place, forming a seven‐membered palladacycle D . Finally, reductive elimination of D and the subsequent dehydrogenative aromatization in the presence of either palladium(0) [21] or palladium (II) catalyst afford the desired product 3 a [22] . However, another pathway cannot be totally excluded at current stage.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Song

Zhang

et al. 2021

Adv Synth Catal

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Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Song

Zhang

et al. 2021

Adv Synth Catal

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“…This gives rubbers local repairing properties and designable mechanical properties. − Watkins et al synthesized 1-(2-furyl)-1,3-butadiene using 3-(2-furyl)-2-propenal, methyltriphenylphosphnium bromide, and sodium hexamethyldisilazane. Subsequently, much effort has been given to the production of F-diene. − Unfortunately, all methods involve uncommon feedstocks (e.g., acryl furan, iodofuran, and dibromopropene), hazardous reagents (e.g., organic phosphine, and Grignard reagents), and large amounts of organic solvents, which are typically nonrenewable chemicals and can cause environmental issues. Additionally, these processes must carry out under an inert atmosphere, and solvents need to be purified and dried.…”

Section: Introductionmentioning

confidence: 99%

Production of a Renewable Functionalized 1,3-Diene from Furfural–Acetone Adduct over Supported Heteropolyacid Catalysts

Liu

et al. 2020

ACS Sustainable Chem. Eng.

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The transformation of renewable feedstocks into high-value chemicals is a sustainable and eco-friendly energy technology. In this work, a functionalized 1,3-diene (1-(2-furyl)-1,3-butadiene, F-diene), with significant importance in high-performance elastomer production, was produced from a furfural–acetone adduct. Heteropolyacids were developed as efficient and eco-friendly catalysts, and a 96% selectivity toward F-diene was obtained. The relationship between catalyst structure and catalytic efficiency (conversion, selectivity, and formation rate) suggests that F-diene production is dependent on both the Keggin structure and the acidity (the amount of Brønsted and Lewis acids) of the catalysts. Linear fitting of the F-diene formation rate and acidity indicates that the catalytic capacity enhancement is linearly correlated with the amount of Brønsted acid sites, and the importance of Lewis acids is also deduced. Finally, Ce species was employed to improve the initial activity of the catalysts and yielded 93% selectivity toward F-diene after 5 h on stream. Thus, a synergistic effect between Brønsted and Lewis acids on this reaction was revealed, especially in the initial stage of the reaction.

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“…We have previously reported that activated-carbon-supported platinum metal catalysts effectively catalyze the dehydrogenation of primary and secondary alcohols in basic aqueous media, , and we have very recently established the Pd/C-catalyzed dehydrogenative aromatization method for cyclohexene and cyclohexadiene derivatives under mild reaction conditions …”

Section: Introductionmentioning

confidence: 99%

Microwave-Mediated Site-Selective Heating of Spherical-Carbon-Bead-Supported Platinum for the Continuous, Efficient Catalytic Dehydrogenative Aromatization of Saturated Cyclic Hydrocarbons

Ichikawa

Matsuo

Tachikawa

et al. 2019

ACS Sustainable Chem. Eng.

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A microwave (MW)-assisted method for the continuous production of hydrogen from methylcyclohexane using platinum on spherical carbon beads has been developed, and its application to the efficient dehydrogenative aromatization of fully saturated cyclic alkanes, including piperidines as representative heterocycles, has been studied. Effective dehydrogenation was achieved by the construction of a highly intense energy field, which acted as a reactive site, on the irradiation of the carbon beads (CB) support. The reaction could be carried out with only 10-W single-frequency MWs. The catalyst system could be used continuously for at least 12 h without any loss of catalyst activity. Dehydrogenative aromatization could also be catalyzed and simple cyclohexane derivatives, as well as piperidine derivatives as representative N-heterocyclic alkanes, were tested.

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Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes

Abstract: Highly-functionalized arenes could be efficiently constructed by Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes.

Cited by 28 publications

References 29 publications

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Production of a Renewable Functionalized 1,3-Diene from Furfural–Acetone Adduct over Supported Heteropolyacid Catalysts

Microwave-Mediated Site-Selective Heating of Spherical-Carbon-Bead-Supported Platinum for the Continuous, Efficient Catalytic Dehydrogenative Aromatization of Saturated Cyclic Hydrocarbons

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