| 95% |
With oxygen; 1-(n-butyl)-3-methylimidazolium triflate at 20℃; for 0.25h; Electrochemical reaction; Green chemistry; |
General procedure for oxidation reactions
General procedure: A mixture of [bmim][OTf] (20 mL) and ketone (0.1 mol) in a three-electrode cell fitted with activated carbon fiber as the anode and Pt cathode was subjected to electro-catalytic oxidation at a constant current at room temperature for an appropriate time. O2 gas was charged into the cell through a O2 bomb to a desired amount at the flow rate of 15 mL min-1. A magnetic stirrer was employed during the electro-oxidation. The progress of the reaction was monitored by GC. After completion of the reaction, the organic phase was extracted with dichloromethane (3×20 mL). The solvent was removed and the residue was purified by preparative thin-layer chromatography on silica gel (ethyl acetate: hexane, 1:10) to afford the desired pure product. The rest of the ionic liquid was recovered. Fresh substrates were then recharged to the recovered electro-catalytic system and then recycled under identical reaction conditions. The target substrates were characterized by Elemental analysis, NMR spectra or compared with their authentic samples. Spectroscopic data for selected products is as follows. 6-Methyltetrahydro-2H-pyran-2-one (Table 3, entry 15). Colourless oil, bp: 111-113 °C/15 mm (Ref. [54] 110-112 °C/15 mm). 1H NMR: δ 1.39 (d, J = 8.0 Hz, CH3, 3H), 1.73-1.89 (m, CH2CH2, 4H), 2.36 (m, CH2, 2H), 4.32 (m, CH, 1H). 13C NMR: δ 19.4, 21.5, 29.8, 71.1, 170.3. Anal. calcd. for C6H10O2: C, 63.13; H, 8.79; O, 28.02. Found: C, 63.14; H, 8.83; O, 28.03. |
| 86% |
With bis-trimethylsilanyl peroxide; 4 A molecular sieve; tin(IV) chloride; rac-diaminocyclohexane In tetrahydrofuran; dichloromethane for 2h; Ambient temperature; |
|
| 80% |
With MoOBr3; dihydrogen peroxide; acetic anhydride; acetic acid at 50 - 70℃; for 6h; |
|
| 80% |
With MoOBr3; dihydrogen peroxide; acetic anhydride; acetic acid at 50 - 70℃; for 6h; liquid-phase catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones; regioselectivity; kinetic study; addition of cyclanones C5-C6 to linear, monocyclic and bicyclic olefins; |
|
| 70% |
With magnesium monoperoxyphthalate hexahydrate In N,N-dimethyl-formamide at 20℃; |
|
| 37% |
With ReCl<SUB>4</SUB>(NCMe)<SUB>2</SUB>; dihydrogen peroxide In water; 1,2-dichloro-ethane at 70℃; for 6h; |
General procedure: In typical conditions, Re catalysts were used as stock solutions (for this, 10.0 mg of the compound 1-10 were dissolved in 2.00 mL of 1,2-dichloroethane, 1,2 DCE). The required amount of this stock solution for the desired oxidant/catalyst molar ratio (1000:1) was transferred to a second flask containing 3.00 mL of 1,2-dichloroethane. 1.7 mmol of H2O2 as a 30% aqueous solution (102 μL) and 1.7 mmol of substrate were then added, and the reaction solution was stirred for 6 h at the desired temperature (typically 70 °C) and normal pressure (dinitrogen atmosphere). Then, 120 μL of cycloheptanone (internal standard) and 10.00 mL of diethyl ether (to extract the substrate and the organic products from the reaction mixture) were added. The obtained mixture was stirred during 10 min and then a sample (1 μL) was taken from the organic phase and analysed by GC using the internal standard method. Blank tests indicate that no oxidation takes place in the absence of the Re catalyst or the oxidant. |
| 25% |
With [ReO3(1,3,5-triaza-7-phosphaadamantane)2][ReO4]; dihydrogen peroxide In 1,2-dichloro-ethane at 70℃; for 6h; Inert atmosphere; regioselective reaction; |
|
| 99 % Chromat. |
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 40℃; for 5h; |
|
| 96 % Chromat. |
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 40℃; for 5h; with/without catalyst; |
|
| 75 % Chromat. |
With dihydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate In water at 60℃; for 24h; |
|
|
With peracetic acid In acetonitrile at 60℃; for 12h; |
|
|
With Sn-Beta-2 zeolite; dihydrogen peroxide In 1,4-dioxane at 80℃; for 8h; |
|
| 100 %Chromat. |
With dihydrogen peroxide In 1,1,1,3',3',3'-hexafluoro-propanol; water at 50℃; for 1.5h; |
|
|
With recombinant cyclohexanone monooxygenase from Acinetobacter sp. NCIMB9871 In methanol at 20℃; for 2h; Enzymatic reaction; regioselective reaction; |
2.3 Biotransformations
General procedure: Whole-cell biotransformations were performed in 40mL amber glass vials using 1mL reaction volumes. The biotransformation reaction mixture (BRM) consisted of 0.1g wet weight/mL in 200mM Tris-HCl (pH 8), 100mM glucose and 100mM glycerol. The reactions were initiated by the addition of substrate (10mM) dissolved in methanol. Reactions were performed at 20°C for 2h, where after the reactions were stopped and extracted using an equal volume (2 times 0.5mL) of ethyl acetate containing 2mM 1-undecanol or 2mM 3-octanol as internal standard. GC-MS analysis was carried out on a Finnigan Trace GC ultra (ThermoScientific) equipped with a FactorFour VF-5ms column (60m×0.32mm×0.25μm, Varian). Chiral separation (Table S2) was performed using either a Chiraldex G-TA or B-TA column (30m×0.25mm×0.12μm, Astec). |
|
With C13H9NO5S(2-)*Sn(4+)*2CH3(1-)*1.5CH4O; dihydrogen peroxide In water at 60℃; for 1h; Sonication; |
|
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