A Stepwise Electrochemical Baeyer–Villiger Oxidation with Water as the Oxygen Source
Baeyer-Villiger oxidation is a method with a 125-year history that produces lactones through a synergistic mechanism by reaction with stoichiometric peracids. Therefore, substituted lactones can be obtained from only substituted cyclic ketones. In this context, an electrochemical Baeyer-Villiger oxidation was developed using a CeO<sub>2</sub>@PbO<sub>2</sub>@Ti electrode, which produces substituted lactones through a stepwise mechanism. PbO<sub>2</sub>, in combination with a benzoic acid molecular catalyst, can generate and utilize reactive oxygen species from electrochemical water splitting to serve as the oxidant. CeO<sub>2</sub> is designed to promote the stepwise mechanism while suppressing the synergistic mechanism. Therefore, substituted lactone can be produced from unsubstituted cyclic ketone with high selectivity (77%) and yield (20 mM) through a carbocation rearrangement process. The developed stepwise electrochemical Baeyer-Villiger oxidation, using water as the oxygen source, offers a new green approach to organic synthesis.
Authors
- Baijing Wu
- Zidong Wei (ORCID: https://orcid.org/0000-0001-8001-9729)
- Minhua Shao (ORCID: https://orcid.org/0000-0003-4496-0057)
- Cunpu Li (ORCID: https://orcid.org/0000-0002-5912-2980)
- Bin Liu (ORCID: https://orcid.org/0000-0002-4685-2052)
- Xiaoxue Luo
- Yufeng Wang (ORCID: https://orcid.org/0009-0008-8710-4641)
- Youdong Wang
Institutions
- Chongqing University (CN)
- City University of Hong Kong (HK)
- Hong Kong University of Science and Technology (HK)
Publication Details
- Journal
- The Journal of Physical Chemistry Letters
- Published
- 2024-10-10
- DOI
- https://doi.org/10.1021/acs.jpclett.4c02342
- Citations
- 5
- Primary Topic
- Catalysis and Oxidation Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.53
Funders
- National Natural Science Foundation of China
- National Key Research and Development Program of China