Multiple deuteration of alkanes synergistically-catalyzed by platinum and rhodium on carbon as a mixed catalytic system

Yamada, Tsuyoshi; Sawama, Yoshinari; Shibata, Kyoshiro; Morita, Kosuke; Monguchi, Yasunari; Sajiki, Hironao

doi:10.1039/c4ra16386a

Cited by 27 publications

(13 citation statements)

References 62 publications

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“…The addition of the catalytic hydroquinone as a polymerization inhibitor could improve the yield (73%) of the desired 1 a – d 3 with excellent D contents (Scheme , bottom reaction formula) along with a trace amount of hydrogenated product (dodecyl propanoate) (See Supporting Information). Although alkanes were also multi deuterated under Pt/C‐catalyzed analogous conditions in i ‐PrOH/D 2 O, the dodecyl group (aliphatic side chain) of 1 a was never deuterated under the present reaction conditions. Meanwhile, the deuteration of dodecyl propanoate as a substrate proceeded at all methyl and methylene groups, while the deuterium efficiency was low (eq.…”

Section: Methodsmentioning

confidence: 78%

Direct Deuteration of Acrylic and Methacrylic Acid Derivatives Catalyzed by Platinum on Carbon in Deuterium Oxide

et al. 2018

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The platinum on carbon (Pt/C)-catalyzed deuteration of acrylic and methacrylic acid derivatives in deuterium oxide (D 2 O) efficiently proceeded to give the corresponding acrylic acid-d 3 and methacrylic acid-d 5 derivatives. The olefinic functionality, as well as the methyl group on the unsaturated functionality of the substrate, were satisfactorily deuterated via the hydrogen (H)deuterium (D) exchange reaction. The obtained deuterated compounds are useful building blocks and efficiently converted to the corresponding desired products including a polymer without the degradation of the original deuterium contents.

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Section: Methodsmentioning

confidence: 78%

Direct Deuteration of Acrylic and Methacrylic Acid Derivatives Catalyzed by Platinum on Carbon in Deuterium Oxide

et al. 2018

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“…In contrast with the Pt/C- and Fe-catalyzed arene reduction, H–D exchange reaction of arenes could proceed without the reduction of arene moiety in the glass flask under the similar reaction conditions using Pt/C in 2-PrOH and D 2 O instead of H 2 O. 13 Therefore, the present phenomenon is valuable to alert the chemists about the effect of reaction apparatus.…”

Section: Introductionmentioning

confidence: 93%

Birch-Type Reduction of Arenes in 2-Propanol Catalyzed by Zero-Valent Iron and Platinum on Carbon

et al. 2019

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Catalytic arene reduction was effectively realized by heating in 2-propanol/water in the presence of Pt on carbon (Pt/C) and metallic Fe. 2-Propanol acted as a hydrogen source, obviating the need for flammable (and hence, dangerous and hard-to-handle) hydrogen gas, while metallic Fe acted as an essential co-catalyst to promote reduction. The chemical states of Pt and Fe in the reaction mixture were determined by X-ray absorption near-edge structure analysis, and the obtained results were used to suggest a plausible reaction mechanism, implying that catalytic reduction involved Pt- and Fe-mediated single-electron transfer and the dehydrogenation of 2-propanol.

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“…[59] Similarly, with a mixture of Pt/ C and Rh/C catalysts, HÀ D exchange of alkanes occurred to produce the corresponding deuterated cyclic and linear alkanes in a mixed i-PrOD-d 8 /D 2 O solvent. [60] The above heterogeneous metal catalysts mainly rely on the electronic action of metals to activate the substrates and deuterium sources. Specifically, depending on the transition metal, the exchange process might follow an associative mechanism or a dissociative mechanism.…”

Section: Heterogeneous Metal Catalystsmentioning

confidence: 99%

Recent Advances in the Synthesis of Deuterium‐Labeled Compounds

2021

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Deuterium‐labeled compounds are of importance in chemical, environmental, and biological fields. Preparation methods for deuterium‐labeled compounds have been studied extensively in response to increasing demand for these chemicals. In this review, we summarize recent advances in synthetic methods and present a comprehensive overview of diverse routes, including conventional deuteration and hydrogen‐deuterium exchange. Deuteration by the classical process, which starts from appropriate available labeled precursors, is introduced for different reaction types. Key features of hydrogen‐deuterium exchange are elaborated in detail from the perspective of the catalyst and the chemical structure of the substrate. Regioselective deuteration at the target position is discussed because of the role of stereospecific deuterium labeling in medicine. Finally, challenges and future prospects of these processes are discussed to provide a general guideline for the synthesis of deuterium‐labeled compounds.

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Multiple deuteration of alkanes synergistically-catalyzed by platinum and rhodium on carbon as a mixed catalytic system

Abstract: A mild and efficient deuterium labeling method of alkanes based on the synergistic effect of Pt–Rh combination was developed.

Cited by 27 publications

References 62 publications

Direct Deuteration of Acrylic and Methacrylic Acid Derivatives Catalyzed by Platinum on Carbon in Deuterium Oxide

Direct Deuteration of Acrylic and Methacrylic Acid Derivatives Catalyzed by Platinum on Carbon in Deuterium Oxide

Birch-Type Reduction of Arenes in 2-Propanol Catalyzed by Zero-Valent Iron and Platinum on Carbon

Recent Advances in the Synthesis of Deuterium‐Labeled Compounds

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