Platinum on carbon-catalysed site-selective H–D exchange reaction of allylic alcohols using alkyl amines as a hydrogen source

Alkyltrimethylammonium chlorides (ATACs) are widely utilized as cationic surfactants in various scientific fields. Furthermore, deuterium‐incorporated compounds can be powerful tools for elucidating the complicated morphologies of molecules with high molecular weights. Dodecyltrimethylammonium chloride (DTAC), as a representative ATAC, underwent the regioselective multi‐deuteration of alkylamine moiety, except for α and β‐positions. Deuteration was performed under Pt/C and Ru/C‐catalyzed conditions in 2‐PrOH and D2O. The stimulated Raman scattering (SRS) revealed the specific signals of multi‐deuterated DTAC in the silent region.

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Unprecedented Regioselective Deuterium‐Incorporation of Alkyltrimethylammonium Chlorides and Raman Analysis

Sawama

Matsuda

Moriyama

et al. 2023

Asian J Org Chem

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Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q

Moriyama,

Mae,

Shibata

et al. 2023

Chem. Commun.

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Transition-Metal-Catalyzed Deuteration via Hydrogen Isotope Exchange

Jiang,

Gao,

Bai

2024

SynOpen

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Direct hydrogen isotope exchange represents a distinctive strategy for deuterium labelling, where the protium is directly replaced by deuterium. In this graphic review, we summarized the progress in deuteration via transition metal catalyzed hydrogen isotope exchange. The review was organized according to the mechanism of C-H bond activation in the homogeneous catalysis, and the heterogeneous catalysis was also discussed according to the catalyst type. Representative mechanistic processes were depicted, and proven cases for tritiation were also highlighted.

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Platinum on carbon-catalysed site-selective H–D exchange reaction of allylic alcohols using alkyl amines as a hydrogen source

Abstract: We developed platinum on carbon-catalysed deuteration reaction of tert-allylic alcohols using deuterium oxide as a deuterium source. Amylamine was dehydrogenated by platinum on carbon to generate an appropriate amount of...

Cited by 4 publications

References 54 publications

Unprecedented Regioselective Deuterium‐Incorporation of Alkyltrimethylammonium Chlorides and Raman Analysis

Unprecedented Regioselective Deuterium‐Incorporation of Alkyltrimethylammonium Chlorides and Raman Analysis

Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q

Transition-Metal-Catalyzed Deuteration via Hydrogen Isotope Exchange

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