Details
| Original language | English |
|---|---|
| Pages (from-to) | 635-642 |
| Number of pages | 8 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 345 |
| Issue number | 5 |
| Publication status | Published - 23 Apr 2003 |
Abstract
A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with α-chirality without racemization. This also includes the synthesis of α-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.
Keywords
- Aldehyde, Aminoaldehyde, Oxidation, Polymer-bound reagent, Radical reaction
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Advanced Synthesis and Catalysis, Vol. 345, No. 5, 23.04.2003, p. 635-642.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Polymer-Supported Bisacetoxybromate(I) Anion - An Efficient Co-Oxidant in the TEMPO-Mediated Oxidation of Primary and Secondary Alcohols
AU - Brünjes, Marco
AU - Sourkouni-Argirusi, Georgia
AU - Kirschning, Andreas
PY - 2003/4/23
Y1 - 2003/4/23
N2 - A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with α-chirality without racemization. This also includes the synthesis of α-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.
AB - A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with α-chirality without racemization. This also includes the synthesis of α-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.
KW - Aldehyde
KW - Aminoaldehyde
KW - Oxidation
KW - Polymer-bound reagent
KW - Radical reaction
UR - http://www.scopus.com/inward/record.url?scp=0242573151&partnerID=8YFLogxK
U2 - 10.1002/adsc.200202208
DO - 10.1002/adsc.200202208
M3 - Article
AN - SCOPUS:0242573151
VL - 345
SP - 635
EP - 642
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 5
ER -