A highly efficient heterogeneous aerobic alcohol oxidation catalyzed by immobilization of bipyridine copper(I) complex in MCM-41

A heterogeneous copper(I)-catalyzed aerobic oxidation of primary benzylic and allylic alcohols to aldehydes was achieved under air in EtOH at 50 °C in the presence of 5 mol% of MCM-41-immobilized bipyridine copper(I) complex [MCM-41-bpy-CuI] and 5 mol% of 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO)...

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Published inTetrahedron Vol. 71; no. 46; pp. 8725 - 8731
Main Authors Zhao, Hong, Chen, Qiurong, Wei, Li, Jiang, Yuanyuan, Cai, Mingzhong
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.11.2015
Elsevier
Subjects
Aerobic alcohol oxidation
Bipyridine ligand
Chemistry
Chemistry, Organic
Heterogeneous catalysis
MCM-41
Physical Sciences
Science & Technology
Supported copper complex
Heterogeneous catalysis
Aerobic alcohol oxidation
MCM-41
Supported copper complex
Bipyridine ligand
HYDROGENATION
MECHANISM
CHITOSAN
ALDEHYDES
GREEN
AMINES
ARYL HALIDES
OLEFINS
RECYCLABLE CATALYST
N-ARYLATION
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Summary:A heterogeneous copper(I)-catalyzed aerobic oxidation of primary benzylic and allylic alcohols to aldehydes was achieved under air in EtOH at 50 °C in the presence of 5 mol% of MCM-41-immobilized bipyridine copper(I) complex [MCM-41-bpy-CuI] and 5 mol% of 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) using aqueous ammonia as base, yielding a variety of aromatic and α,β-unsaturated aldehydes in good to excellent yields. This heterogeneous copper catalyst can be easily recovered by a simple filtration of reaction solution and reused for at least 10 consecutive trials without any decreases in activity. The use of recyclable heterogeneous copper catalyst and green reagents, such as air as oxidant and ethanol as solvent, made the system attractive for environmentally sustainable processes. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.09.054