Copper-Mediated Selective Oxidation of a CH Bond

An environmentally friendly procedure has been developed for the oxidation of 2,4,6‐trimethylphenol (TMP) at the para C sp 3–H bond. Upon reaction with H2O2 in the presence of catalytic amounts of CuII and neocuproine in methanol at 65 °C, 4‐(methoxymethyl)‐2,6‐dimethylphenol (MDP) or 4‐hydroxy‐3,5‐...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 44; no. 23; pp. 3585 - 3587
Main Authors Boldron, Christophe, Gamez, Patrick, Tooke, Duncan M., Spek, Anthony L., Reedijk, Jan
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 06.06.2005
WILEY‐VCH Verlag
Wiley
Subjects
biomimetic synthesis
Carbon - chemistry
Chemistry
Chemistry, Multidisciplinary
copper
Copper - chemistry
CH activation
homogeneous catalysis
Hydrogen - chemistry
Hydrogen Bonding
oxidation
Oxidation-Reduction
Physical Sciences
Science & Technology
SYSTEM
COMPLEX CATALYST
DIOXYGEN
C-H activation
homogeneous catalysis
PHENOLS
oxidation
copper
2,4,6-TRIMETHYLPHENOL
biomimetic synthesis
MOLECULAR-OXYGEN
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Summary:An environmentally friendly procedure has been developed for the oxidation of 2,4,6‐trimethylphenol (TMP) at the para C sp 3–H bond. Upon reaction with H2O2 in the presence of catalytic amounts of CuII and neocuproine in methanol at 65 °C, 4‐(methoxymethyl)‐2,6‐dimethylphenol (MDP) or 4‐hydroxy‐3,5‐dimethylbenzaldehyde (HDB) is formed (see reaction).
Bibliography:istex:5EBF474310418BAAB558DC29F5511F59027CB77D
ark:/67375/WNG-C2KPZCXD-7
Financial support from COST Action (D21/003/2001) and the Dutch National Research School Combination Catalysis (HRSMC and NIOK) is thankfully acknowledged.
ArticleID:ANIE200462946
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200462946