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Synlett
DOI: 10.1055/s-0043-1773545
DOI: 10.1055/s-0043-1773545
letter
Accelerating Effect of the Addition of HFIP on the Oxidation of Alcohols Using TEMPO/PIDA
This study was supported by Japan Society for the Promotion of Science (MEXT KAKENHI grant 21K06487) (to S.H.).
Abstract
The accelerating effect of the addition of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) on the oxidation of alcohols using 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) in combination with phenyliodine(III) diacetate (PIDA) was investigated. HFIP accelerates the oxidation of primary and secondary alcohols that are not sterically hindered. Based on the results in this study, the acceleration effect of HFIP may be due to the acceleration of the re-oxidation step by PIDA.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773545.
- Supporting Information
Publikationsverlauf
Eingereicht: 04. April 2025
Angenommen nach Revision: 25. April 2025
Artikel online veröffentlicht:
04. Juni 2025
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References and Notes
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- 15 3-Phenylpropanal (2b); Typical Procedure To a mixture of 1b (136 mg, 1.00 mmol), TEMPO (15.6 mg, 100 μmol), and HFIP (105 μL, 1.00 mmol) in DCM (10 mL) was added PIDA (483 mg, 1.50 mmol), and the mixture was stirred at r.t. for 1.5 h. The reaction was quenched with sat. aq. NaHCO3 and extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to give a residue. The residue was purified by MPLC (n-hexane/AcOEt = 1:0 to 4:1) to give 2b (117 mg, 87%) as a colorless oil.16 1H NMR (400 MHz, CDCl3): δ = 9.84–9.81 (m, 1H), 7.34–7.27 (m, 2H), 7.25–7.17 (m, 3H), 2.98 (t, J = 7.2 Hz, 2H), 2.80 (t, J = 7.5 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ = 201.7, 140.4, 128.7, 128.4, 126.4, 45.3, 28.2.
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For selected reviews, see: