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Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols
Author(s) -
Brünjes Marco,
SourkouniArgirusi Georgia,
Kirschning Andreas
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200202208
Subject(s) - chemistry , benzaldehyde , reagent , hypochlorite , alcohol oxidation , bromate , catalysis , racemization , organic chemistry , primary (astronomy) , catalytic oxidation , metal ions in aqueous solution , solvent , oxidizing agent , metal , polymer chemistry , ion , physics , astronomy
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.