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Peer-reviewedCC BYThe Journal of organic chemistry

Alpha-Oxygenation of Ketones Using TEMPO Disproportionation.

  • Madison A Chupela1
  • Jeremy M Williamson1
  • Brett N Hemric1
  1. 1Department of Chemistry and Biochemistry, University of Tampa, Tampa, Florida33606, United States.
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Abstract

The alpha-oxygenation of ketones via acid-driven TEMPO disproportionation is reported. This straightforward and robust protocol from simple starting materials exhibits an excellent substrate scope in terms of scaffold substitutions, selectivity, and functional group tolerance, with substrate limitations elucidated and highlighted. Furthermore, the mechanism was probed by way of UV-visible spectroscopy, deuterium scrambling experiments, kinetic isotope effect, and Hammett analysis to illustrate the reaction dynamics.

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Cite

BibTeXRIS
BibTeX
@article{chupela2026alphaoxygenation,
  title = {{Alpha-Oxygenation of Ketones Using TEMPO Disproportionation.}},
  author = {Madison A Chupela and Jeremy M Williamson and Brett N Hemric},
  journal = {The Journal of organic chemistry},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.joc.6c01554},
  url = {https://europepmc.org/article/MED/42917596},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Alpha-Oxygenation of Ketones Using TEMPO Disproportionation.
AU  - Madison A Chupela
AU  - Jeremy M Williamson
AU  - Brett N Hemric
PY  - 2026
DA  - 2026/10/01
JO  - The Journal of organic chemistry
DO  - 10.1021/acs.joc.6c01554
UR  - https://europepmc.org/article/MED/42917596
AB  - The alpha-oxygenation of ketones via acid-driven TEMPO disproportionation is reported. This straightforward and robust protocol from simple starting materials exhibits an excellent substrate scope in terms of scaffold substitutions, selectivity, and functional group tolerance, with substrate limitations elucidated and highlighted. Furthermore, the mechanism was probed by way of UV-visible spectroscopy, deuterium scrambling experiments, kinetic isotope effect, and Hammett analysis to illustrate the reaction dynamics.
SN  - 0022-3263
SN  - 1520-6904
ER  -