Mild and Direct Multiple Deuterium‐Labeling of Saturated Fatty Acids

Yamada, Tsuyoshi; Park, Kwihwan; Yasukawa, Naoki; Morita, Kosuke; Monguchi, Yasunari; Sawama, Yoshinari; Sajiki, Hironao

doi:10.1002/adsc.201600363

Cited by 25 publications

(10 citation statements)

References 52 publications

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“…Numerous methods using homogeneous and heterogeneous catalysis for the H/D exchange of various functionalized molecules have been described. For example, the exchange of aromatic, heteroaromatic, vinylic, allylic, or aliphatic protons and the exchange of protons of a C–H bond adjacent to a heteroatom have been reported. In this field, a major breakthrough was achieved by Pieters and co-workers in 2015, who reported an enantiospecific deuteration of amino acids through C–H activation using ruthenium nanocatalyst .…”

Section: Introductionmentioning

confidence: 99%

Development and Scale-Up of Stereoretentive α-Deuteration of Amines

Michelotti¹,

Rodrigues²,

Roche³

2017

Org. Process Res. Dev.

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A stereoretentive deuteration of amino acids and amines has been developed using ruthenium on carbon catalyst, hydrogen gas at atmospheric pressure, and deuterium oxide as a source of deuterium. The process was successfully scaled-up, avoiding the use of expensive and sensitive catalyst and avoiding the use of deuterium gas under pressure. High deuterium incorporation and high yield of labeled compounds were obtained by a simple filtration process.

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Section: Introductionmentioning

confidence: 99%

Development and Scale-Up of Stereoretentive α-Deuteration of Amines

Michelotti¹,

Rodrigues²,

Roche³

2017

Org. Process Res. Dev.

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“…Various catalytic systems have been developed to perform HÀ D exchange over acids. Yamada et al [101] developed a carbon-supported platinum catalyst and catalyzed the deuteration of multiple saturated fatty acids. In the presence of a mixed deuterium oxide and isopropyl alcohol solvent, excellent deuterium efficiency was achieved at 120 °C.…”

Section: Carbonyl Compoundsmentioning

confidence: 99%

“…Various catalytic systems have been developed to perform H−D exchange over acids. Yamada et al [101] . developed a carbon‐supported platinum catalyst and catalyzed the deuteration of multiple saturated fatty acids.…”

Section: H−d Exchangementioning

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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“…The present in situ-generation method of H 2 from i-PrOH (Chart 9) can also be applied to the H-D exchange reaction of arenes 46) and carboxylic acids 47) using Pt/C 48) in the mixed solvent of i-PrOH and D 2 O, and the corresponding multideuterated products are efficiently obtained (Chart 10). Since only a tiny but sufficient amount of H 2 for the activation of Pt/C is generated during the deuteration, the hydrogenation of the coexisting reducible functionalities (e.g., olefin, ketone, etc.)…”

Section: H-d Exchange Reaction Using Isopropanol As a Hydrogen Sourcementioning

confidence: 99%

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

et al. 2018

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Deuterium-labeled compounds are widely utilized in various scientific fields. We summarize the recent advances in the direct deuteration of sugar, saturated fatty acid, and arene derivatives using heterogeneous platinum group metal on carbon catalysts by our research group. Hydrogen gas is a key catalyst-activator to facilitate the present H-D exchange reactions. In this review, the direct activation method of catalysts using in situ-generated hydrogen based on the dehydrogenation of alcohols is introduced. The obtained multiple deuterium-labeled products, including bioactive compounds, are expected to contribute to the development of many scientific investigations.

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Mild and Direct Multiple Deuterium‐Labeling of Saturated Fatty Acids

Cited by 25 publications

References 52 publications

Development and Scale-Up of Stereoretentive α-Deuteration of Amines

Development and Scale-Up of Stereoretentive α-Deuteration of Amines

Recent Advances in the Synthesis of Deuterium‐Labeled Compounds

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

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