1999
DOI: 10.1055/s-1999-2857
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Ytterbium(III) Triflate as a Recyclable Catalyst for the Selective Atom Economic Oxidation of Benzyl Alcohols to Benzaldehydes

Abstract: Ytterbium(III) triflate (10mol%) was found to catalyse the selective oxidation of a range of simple benzyl alcohols to benzaldehydes in good to excellent yield using a stoichiometric quantity of 69% nitric acid as the oxidant, and where the only by-products were water and oxides of nitrogen. The catalyst can be readily recovered and recycled by a simple evaporative process.The selective oxidation of benzylic alcohols to benzaldehydes is a transformation of considerable importance in organic synthesis. Whilst n… Show more

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Cited by 15 publications
(12 citation statements)
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“…The reaction of hydroxy benzoins (1-7) and benzils (8)(9)(10)(11)(12)(13)(14) with TABG then hydrolysis of acetyl group yielded benzoin-D-glucosides (15)(16)(17)(18)(19)(20) and benzil-D-glucosides (22)(23)(24)(25), respectively [21][22]. Observation of the anomeric proton coupling constant value around J = 7-8 Hz in the 1 H NMR spectrum of the synthesized benzoin/benzil-O-β-D-glucosides shows that the D-glucose unit was in the β form.…”
Section: Resultsmentioning
confidence: 99%
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“…The reaction of hydroxy benzoins (1-7) and benzils (8)(9)(10)(11)(12)(13)(14) with TABG then hydrolysis of acetyl group yielded benzoin-D-glucosides (15)(16)(17)(18)(19)(20) and benzil-D-glucosides (22)(23)(24)(25), respectively [21][22]. Observation of the anomeric proton coupling constant value around J = 7-8 Hz in the 1 H NMR spectrum of the synthesized benzoin/benzil-O-β-D-glucosides shows that the D-glucose unit was in the β form.…”
Section: Resultsmentioning
confidence: 99%
“…When the activities of all compounds according to FRAP, CUPRAC and DPPH were examined, it was seen that compound 20 for FRAP, compound 5 for CUPRAC, and compound 14 for DPPH were the most effective antioxidant compounds. The antioxidant activities for the benzil-O-β-D-glucoside (21)(22)(23)(24)(25) showed that compound 25 was the most effective for FRAP (2570.42 ± 25.01 μg/mL Trolox/gram DW) and the compound 23 was the most active to CUPRAC (273.67 ± 27.23, μg.mL -1 Trolox/gram DW) and DPPH (17.74 ± 0.35, mg/mL) methods. When looking at the substitution positions of these compounds, it has been found that they are generally more effective when they are substituted at the 3-position.…”
Section: Resultsmentioning
confidence: 99%
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“…11 Among other oxidation agents, nitric acid has attracted much attention in the conversion of alcohols into carbonyl compounds mainly due to its ready availability and strong oxidizing power. The reaction sys-tems of aqueous 20% nitric acid-nitromethane, 12 nitric acid-dichloromethane, 13 nitric acid-ytterbium(III) triflate-1,2-dichloroethane 14 and sodium nitrate-p-toluenesulfonic acid 15 have been successfully utilized for the oxidation of alcohols. However, all of these oxidative methods suffer from one or more drawbacks including the use of toxic heavy metal reagents, long reaction times, low yields and inconvenient work-up procedures.…”
mentioning
confidence: 99%