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Iron‐Catalysed Selective Aerobic Oxidation of Alcohols to Carbonyl and Carboxylic Compounds
Author(s) -
Lagerblom Kalle,
Wrigstedt Pauli,
Keskiväli Juha,
Parviainen Arno,
Repo Timo
Publication year - 2016
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201600240
Subject(s) - alcohol oxidation , chemistry , carboxylic acid , alcohol , deoxygenation , primary (astronomy) , steric effects , organic chemistry , aldehyde , catalysis , physics , astronomy
A method for aerobic alcohol oxidation catalysed by Fe(NO 3 ) 3 /2,2’‐bipyridine/TEMPO has allowed highly selective conversion of primary alcohols into either aldehydes or carboxylic acids in one‐step. The oxidation of primary alcohols proceeded selectively to aldehydes, as TEMPO was present in the reaction. Nevertheless, the aldehydes were further oxidized into carboxylic acids as the reaction time was extended. Detailed investigation of the reaction suggested, that the deoxygenation of TEMPO into TMP enabled the auto‐oxidation of aldehydes to carboxylic acids, which was initially inhibited in the presence of TEMPO. The procedure was also efficient in oxidation of secondary alcohols when TEMPO was replaced by the less sterically hindered ABNO.