Electrochemical Oxidation of Benzyl Alcohols via Hydrogen Atom Transfer Mediated by 2,2,2-Trifluoroethanol

We report a novel electrochemical oxidation of benzyl alcohols. We found that trifluoroethanol plays a role as a hydrogen atom transfer (HAT) mediator, enabling the oxidation of electron-deficient substrates that are difficult to directly oxidize on electrode surfaces. Density functional theory calculations, cyclic voltammetry measurements, and constant potential electrolysis studies supported the proposed HAT mechanism. Moreover, the obtained carbonyl compounds could be functionalized in an electrochemical one-pot manner, further highlighting their synthetic utility.

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Publication Details

Journal
Organic Letters
Published
2025-04-30
DOI
https://doi.org/10.1021/acs.orglett.5c01138
Citations
1
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.94

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article

Electrochemical Oxidation of Benzyl Alcohols via Hydrogen Atom Transfer Mediated by 2,2,2-Trifluoroethanol

Takahiro Kawajiri, Satoshi Goda, Eisuke F. Sato, Masahiro Hosoya et al.
1 citations
Organic Letters
Oxidative Organic Chemistry Reactions
0.94
article

Electrochemical Oxidation of Benzyl Alcohols via Hydrogen Atom Transfer Mediated by 2,2,2-Trifluoroethanol

Takahiro Kawajiri, Satoshi Goda, Eisuke F. Sato, Masahiro Hosoya, Seiji Suga
article en
1 citations

Abstract

We report a novel electrochemical oxidation of benzyl alcohols. We found that trifluoroethanol plays a role as a hydrogen atom transfer (HAT) mediator, enabling the oxidation of electron-deficient substrates that are difficult to directly oxidize on electrode surfaces. Density functional theory calculations, cyclic voltammetry measurements, and constant potential electrolysis studies supported the proposed HAT mechanism. Moreover, the obtained carbonyl compounds could be functionalized in an electrochemical one-pot manner, further highlighting their synthetic utility.

Organic LettersVol. 27(18)
Okayama University (JP), Shionogi (Japan) (JP), Futaba (Japan) (JP)
Ministry of Education, Culture, Sports, Science and Technology, Shionogi, Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 27%
Oxidative Organic Chemistry Reactions
0.94
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