A convenient alternative for the selective oxidation of alcohols by silica supported TEMPO using dioxygen as the final oxidant

[Display omitted] •Unconventional oxidation of alcohols to the corresponding aldehydes or ketones.•Clean reactions with minimal work-up in high yields, at room temperature.•Supported TEMPO free radical as heterogeneous catalyst.•First time nitrosonium tetrafluoroborate used as cocatalyst.•Mechanisti...

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Bibliographic Details
Published in:Tetrahedron letters 2015-12, Vol.56 (49), p.6878-6881
Main Authors: Shakir, Ahmed Juwad, Paraschivescu, Codruta, Matache, Mihaela, Tudose, Madalina, Mischie, Alice, Spafiu, Felicia, Ionita, Petre
Format: Article
Language:English
Subjects:
Alcohols oxidation
Mechanism
Nitrosonium tetrafluoroborate
Silica
TEMPO free radical
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Summary:[Display omitted] •Unconventional oxidation of alcohols to the corresponding aldehydes or ketones.•Clean reactions with minimal work-up in high yields, at room temperature.•Supported TEMPO free radical as heterogeneous catalyst.•First time nitrosonium tetrafluoroborate used as cocatalyst.•Mechanistic pathway involves nitrogen oxides and oxoammonium ions. Various primary and secondary alcohols were selectively oxidized to the corresponding aldehydes and ketones using silica supported TEMPO as a heterogeneous catalyst and nitrosonium tetrafluoroborate as a cocatalyst. No over-oxidation of aldehydes to acids, nitration processes or oxidation of double bonds was observed. The reported procedure is very convenient, and uses mild experimental conditions (room temperature and dioxygen as the terminal oxidant). Furthermore, the reactions proceeded cleanly and the isolation of the desired compounds required minimal work-up. A mechanistic pathway has been proposed, in which nitrogen oxides and oxoammonium ions act as an electron transfer double bridge.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.10.099