New Gateways to the Platinum Group Metal-Catalyzed Direct Deuterium-Labeling Method Utilizing Hydrogen as a Catalyst Activator

Sawama, Yoshinari; Park, Kwihwan; Yamada, Tsuyoshi; Sajiki, Hironao

doi:10.1248/cpb.c17-00222

Cited by 35 publications

(14 citation statements)

References 71 publications

(66 reference statements)

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“…As shown in Table 1, we assessed the reaction conditions based on two criteria: total current efficiency and molar selectivity for semihydrogenation. First, we used a combination of Pt cathode and anode catalysts (entries 1-3) because Pt catalysts are commonly used in hydrogenation reactions (Sawama et al, 2018). We found that Pt electrocatalysts can provide high current efficiency, but the selectivity for the Z-alkene (cis-stilbene, 2) against the alkane (dibenzyl, 3), which can be generated by an over-reduction of 2, was moderate.…”

Section: Resultsmentioning

confidence: 99%

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

et al. 2022

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Owing to its applicability in sustainable engineering, flow electrochemical synthesis in a proton-exchange membrane (PEM) reactor has attracted considerable attention. Because the reactions in PEM reactors are performed under electro-organic and flow-synthetic conditions, a higher number of reaction parameters exist compared to ordinary reactions. Thus, the optimization of such reactions requires significant amounts of energy, time, chemical and human resources. Herein, we show that the optimization of alkyne semihydrogenation in PEM reactors can be facilitated by means of Bayesian optimization, an applied mathematics strategy. Applying the optimized conditions, we also demonstrate the generation of a deuterated Z-alkene.

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Section: Resultsmentioning

confidence: 99%

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

et al. 2022

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“…D 2 O has been frequently used in combination with acid catalysts for the deuteration of benzene rings 12,26,35,40 . Recently, Sajiki and coworkers have developed a hydrogen–deuterium exchange reaction using D 2 O as a deuterium source in the presence of platinum‐group catalysts 41–43 . This method can deuterate not only arenes but also saturated aliphatic compounds.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of deuterium‐labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica

Watanabe

Nishitani

Koeduka

2021

Labelled Comp Radiopharmac

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Cinnamic acids are widely distributed in plants, including crops for human use, and exhibit a variety of activities that are beneficial to human health. They also occupy a pivotal position in the biosynthesis of phenylpropanoids such as lignins, anthocyanins, flavonoids, and coumarins. In this context, deuterium‐labeled cinnamic acids have been used as tracers and internal standards in food and medicinal chemistry as well as plant biochemistry. Therefore, a concise synthesis of deuterium‐labeled cinnamic acids would be highly desirable. In this study, we synthesized deuterium‐labeled cinnamic acids using readily available deuterium sources. We also investigated a hydrogen–deuterium exchange reaction in an ethanol‐d1/Et3N system. This method can introduce deuterium atoms at the ortho and para positions of the phenolic hydroxy groups as well as at the C‐2 position of alkyl cinnamates and is applicable to various phenolic compounds. Using the synthesized labeled compounds, we demonstrated that the benzenoid volatiles, such as 4‐methoxybenzaldehyde, in the scent of the flowers of the Japanese loquat Eriobotrya japonica are biosynthesized from phenylalanine via cinnamic and 4‐coumaric acids. This study provides easy access to a variety of deuterium‐labeled (poly)phenols, as well as to useful tools for studies of the metabolism of cinnamic acids in living systems.

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“…For a more detailed account of the work conducted by the Sawama group, please refer to a 2017 review article published by Sawama et al…”

Section: Platinum and Palladiummentioning

confidence: 94%

Highlights of C (sp²)–H hydrogen isotope exchange reactions

Hesk

2019

Labelled Comp Radiopharmac

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The highlights of C (sp 2 )-H hydrogen isotope exchange (HIE) methods developed over the past 10 years are summarized in this review. Major developments include improved Ir(I) catalysts with greater functional group and solvent compatibility and the development of novel base metal catalysts for HIE. In addition, a number of novel Ru-based catalysts have been developed with promising activity. In the area of Pt-and Pd-catalysed exchange, in addition to new advances on heterogeneous Pt-and Pd-catalysed HIE by Sajiki and Shevchenko, a number of groups have reported on homogenous catalysts of Pt and Pd that show an interesting activity and selectivity.

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New Gateways to the Platinum Group Metal-Catalyzed Direct Deuterium-Labeling Method Utilizing Hydrogen as a Catalyst Activator

Cited by 35 publications

References 71 publications

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

Synthesis of deuterium‐labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica

Highlights of C (sp²)–H hydrogen isotope exchange reactions

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New Gateways to the Platinum Group Metal-Catalyzed Direct Deuterium-Labeling Method Utilizing Hydrogen as a Catalyst Activator

Cited by 35 publications

References 71 publications

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

Synthesis of deuterium‐labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica

Highlights of C (sp2)–H hydrogen isotope exchange reactions

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Highlights of C (sp²)–H hydrogen isotope exchange reactions