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Volumn , Issue 4, 2007, Pages 563-566

m-iodosylbenzoic acid as a convenient recyclable reagent for highly efficient RuCl3-catalyzed oxidation of alcohols to carbonyl compounds

(4) Yusubov, Mekhman S a,b Gilmkhanova, Marina P a,b Zhdankin, Viktor V c Kirschning, Andreas d

a NATIONAL RESEARCH TOMSK POLYTECHNIC UNIVERSITY (Russian Federation)

b SIBERIAN STATE MEDICAL UNIVERSITY (Russian Federation)

c UNIVERSITY OF MINNESOTA DULUTH (United States)

d LEIBNIZ UNIVERSITY HANNOVER (Germany)

Author keywords

Catalysis; Hypervalent iodine; m iodosobenzoic acid; Oxidation; Scavenger

Indexed keywords

2 IODOBENZOIC ACID; 2 IODOSYLBENZOIC ACID; 2,4 DINITROPHENYL HYDRAZONE; ACETONITRILE; ALCOHOL DERIVATIVE; ARYL IODIDE; BENZOIC ACID DERIVATIVE; BICARBONATE; CARBONYL DERIVATIVE; HYDRAZONE DERIVATIVE; HYDROXIDE; IODINE DERIVATIVE; MENTHOL; SCAVENGER; UNCLASSIFIED DRUG;

ACIDIFICATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ION EXCHANGE; OXIDATION; RECYCLING;

EID: 33947228565 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970742 Document Type: Article

Times cited : (29)

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- Improved Procedure for the Preparation of m- Iodosylbenzoic Acid (2, m-Iodobenzoic acid (1; 2.48 g, 10 mmol) was added at 40°C to a freshly prepared solution of peracetic acid in AcOH [prepared by stirring a mixture of Ac2O (60 mL) and 35% H 2O2 (14 mL) at 40°C for 4 h in dark] and the resulting mixture was stirred for 12 h at ambient temperature in dark. A spontaneous heating of the reaction mixture up to 45°C and complete dissolution of m-iodobenzoic acid was observed during the first two hours of stirring. The reaction mixture was poured onto ice-water (150 mL, and allowed to crystallize. The precipitate was filtered on a Büchner funnel and washed with ice-water (200 mL, The solid was then dried, first by maintaining suction and then in vacuum, to afford product 2 as a light yellow powder. Yield: 1.90-2.11 g (72-80% yield, mp 168-169°C. 1H NMR 200 MHz, CD3
- 3 (263.93): C, 31.84; H, 1.91. Found: C, 31.77; H, 1.84.

39
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- RuCl3-Catalyzed Oxidation of Alcohols to Carbonyl Compounds: Method A: To a mixture of alcohol (0.05-0.20 mmol) and m-iodosylbenzoic acid (2; 0.075-0.300 mmol, 1.5 equiv) in aq MeCN (MeCN-H2O, 5:1; 0.5-2 mL) an aqueous solution of RuCl3 (1.0-4.0 μL of 0.25 M solution; 0.25-1.0 μmol) was added under stirring at r.t. An instantaneous formation of a cotton-like, off-white precipitate was observed. The reaction mixture was stirred for a period of time indicated in Figures 1 and 2 (the reactions were monitored by TLC, Then, CH 2Cl2 (1.5 mL) and IRA 900 (hydroxide form; 160-620 mg) were added and the mixture was stirred for 5 min. The polymer was removed by filtration and the solution was concentrated under vacuum to afford the NMR-pure carbonyl compound. Most products were additionally identified as 2,4-dinitrophenylhydrazones, prepared by the treatment of reaction mixtures with a standard solution of 2,4-din
- 2O from the extract; most prepared carbonyl compounds were additionally identified as their 2,4-dinitrophenylhydrazones. The aqueous solution that was left after extraction was acidified with HCl, and the white precipitate of m-iodobenzoic acid was separated by filtration and used for regeneration of reagent 2.

40
- 33947269398
- In one case we encountered further oxidation to galacturonic acid when 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was employed (Scheme 2). (Chemical Equation Presented)
- In one case we encountered further oxidation to galacturonic acid when 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was employed (Scheme 2). (Chemical Equation Presented)

41
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- This is particularly well demonstrated for the formation of ulose 4r which can undergo facile elimination of methanol to the corresponding enulose
- This is particularly well demonstrated for the formation of ulose 4r which can undergo facile elimination of methanol to the corresponding enulose.

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