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.
Authors
- Takahiro Kawajiri (ORCID: https://orcid.org/0000-0003-1764-7102)
- Satoshi Goda
- Eisuke F. Sato (ORCID: https://orcid.org/0000-0001-6784-138X)
- Masahiro Hosoya (ORCID: https://orcid.org/0000-0001-9605-9848)
- Seiji Suga (ORCID: https://orcid.org/0000-0003-0635-2077)
Institutions
- Okayama University (JP)
- Shionogi (Japan) (JP)
- Futaba (Japan) (JP)
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
Funders
- Ministry of Education, Culture, Sports, Science and Technology
- Shionogi
- Japan Society for the Promotion of Science