10.1002/cctc.201800438
ChemCatChem
FULL PAPER
Method C for oxidation of secondary alcohols 1l-1n: Mn(NO3)2 ∙4ꢀH2O
(10.0 mg 0.04 mmol), 2-picolinic acid (7.4 mg 0.06 mmol), ABNO (2.8 mg,
0.02 mmol), NaNO3 (10.2 mg, 0.12mmol) and glacial AcOH (4 mL) were
added, in this order, to a 30 mL test tube equipped with a magnetic stirring
bar. The resulting solution was stirred in open air for 5 minutes and the
desired alcohol (2 mmol) was then added. Stirring (800 rpm) was
continued at room temperature until the reaction was completed
(monitored by TLC). Upon completion, the reaction solution was diluted
with diethyl ether (20 mL), followed by washing with water (3×10 mL) to
remove the catalyst. Aqueous phases were combined and extracted with
diethyl ether (1×10 ml). Organic phases were then combined, dried with
MgSO4 and evaporated in vacuo to afford ketones 2l-2n. No further
purification was required.
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Catalyst recycling
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Oxidation of benzyl alcohol for catalyst recycling experiments was
conducted according to the following protocol: Mn(NO3)2 ∙4ꢀH2O (50.2 mg
0.2 mmol), 2-picolinic acid (36.9 mg 0.3 mmol), TEMPO (31.3 mg, 0.2
mmol), NaNO3 (51.0 mg, 0.6 mmol) and AcOH (20 mL) were added, in this
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AcOH (20 ml) were added on top of the catalyst and the formed mixture
was stirred for 5 min. New reaction was then initiated by adding benzyl
alcohol (1.04 ml, 10 mmol). Note: the recycled catalyst should be dried
under oil pump vacuum until the color changes from yellow to dark green.
The use of wet catalyst leads to hampered reactivity.
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We thank Kjell Knapas for his help in the preparation of the
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Keywords: oxidation • alcohols • manganese • synthetic
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