Details
| Original language | English |
|---|---|
| Pages (from-to) | 1423-1434 |
| Number of pages | 12 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 347 |
| Issue number | 10 |
| Publication status | Published - Aug 2005 |
Abstract
Hypochlorite and chlorite exchange resins are evaluated as co-oxidants or oxidants, respectively, for the oxidation of alcohols to the corresponding aldehydes, ketones or carboxylic acids. Polymer-bound hypochlorite can act as a co-oxidant in TEMPO-mediated oxidations of alcohols. The formation of aldehydes only works under weakly acidic conditions. However, the cheap hypochlorite exchange resin is less efficient as co-oxidant compared to the use of ionically immobilised bisacetoxybromate(I) anions. In contrast, the chlorite exchange resin is a highly potent co-oxidant for the preparation of carboxylic acids from the corresponding primary alcohols in the presence of TEMPO. It is demonstrated that in this case also the resin acts as a polymer-bound co-oxidant for both oxidation steps. Yields are commonly excellent as is also demonstrated for examples taken from natural product synthesis which include acid labile glycosides. In most cases, work-up of this heavy metal-free oxidation is kept to a minimum. It often includes filtration followed by removal of the solvent.
Keywords
- Aldehydes, Carboxylic acids, Chlorites, Ketones, Oxidations, Polymer-bound reagents, TEMPO
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Advanced Synthesis and Catalysis, Vol. 347, No. 10, 08.2005, p. 1423-1434.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Practical TEMPO-mediated oxidation of alcohols using different polymer-bound co-oxidants
AU - Kloth, Katrin
AU - Brünjes, Marco
AU - Kunst, Eike
AU - Jöge, Thomas
AU - Gallier, Florian
AU - Adibekian, Alexander
AU - Kirschning, Andreas
PY - 2005/8
Y1 - 2005/8
N2 - Hypochlorite and chlorite exchange resins are evaluated as co-oxidants or oxidants, respectively, for the oxidation of alcohols to the corresponding aldehydes, ketones or carboxylic acids. Polymer-bound hypochlorite can act as a co-oxidant in TEMPO-mediated oxidations of alcohols. The formation of aldehydes only works under weakly acidic conditions. However, the cheap hypochlorite exchange resin is less efficient as co-oxidant compared to the use of ionically immobilised bisacetoxybromate(I) anions. In contrast, the chlorite exchange resin is a highly potent co-oxidant for the preparation of carboxylic acids from the corresponding primary alcohols in the presence of TEMPO. It is demonstrated that in this case also the resin acts as a polymer-bound co-oxidant for both oxidation steps. Yields are commonly excellent as is also demonstrated for examples taken from natural product synthesis which include acid labile glycosides. In most cases, work-up of this heavy metal-free oxidation is kept to a minimum. It often includes filtration followed by removal of the solvent.
AB - Hypochlorite and chlorite exchange resins are evaluated as co-oxidants or oxidants, respectively, for the oxidation of alcohols to the corresponding aldehydes, ketones or carboxylic acids. Polymer-bound hypochlorite can act as a co-oxidant in TEMPO-mediated oxidations of alcohols. The formation of aldehydes only works under weakly acidic conditions. However, the cheap hypochlorite exchange resin is less efficient as co-oxidant compared to the use of ionically immobilised bisacetoxybromate(I) anions. In contrast, the chlorite exchange resin is a highly potent co-oxidant for the preparation of carboxylic acids from the corresponding primary alcohols in the presence of TEMPO. It is demonstrated that in this case also the resin acts as a polymer-bound co-oxidant for both oxidation steps. Yields are commonly excellent as is also demonstrated for examples taken from natural product synthesis which include acid labile glycosides. In most cases, work-up of this heavy metal-free oxidation is kept to a minimum. It often includes filtration followed by removal of the solvent.
KW - Aldehydes
KW - Carboxylic acids
KW - Chlorites
KW - Ketones
KW - Oxidations
KW - Polymer-bound reagents
KW - TEMPO
UR - http://www.scopus.com/inward/record.url?scp=24644464759&partnerID=8YFLogxK
U2 - 10.1002/adsc.200505005
DO - 10.1002/adsc.200505005
M3 - Article
AN - SCOPUS:24644464759
VL - 347
SP - 1423
EP - 1434
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 10
ER -