Aerobic oxidation of alcohols to carbonyl compounds mediated by poly(ethylene glycol)-supported TEMPO radicals

被引:72
作者
Benaglia, M
Puglisi, A
Holczknecht, O
Quici, S
Pozzi, G
机构
[1] CNR, Ist Sci & Tecnol Mol, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
关键词
alcohols; aldehydes; ketones; oxidation; soluble polymers;
D O I
10.1016/j.tet.2005.07.107
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two poly(ethylene glycol)-supported TEMPO (PEG-TEMPO) has been successfully applied as soluble, recyclable catalysts in the chemoselective oxidation of primary and benzylic alcohols with molecular oxygen in the presence of Co(NO3)(2) and Mn(NO3)(2) as co-catalysts (Minisci's conditions). Under those conditions, secondary alcohols are also oxidized to ketones, although usually in lower yields. The insertion of a spacer between the PEG moiety and TEMPO has beneficial effects on both the activity and ease of recovery of the supported catalyst. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:12058 / 12064
页数:7
相关论文
共 58 条
[51]   Organocatalytic oxidations mediated by nitroxyl radicals [J].
Sheldon, RA ;
Arends, IWCE .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1051-1071
[52]   Green, catalytic oxidations of alcohols [J].
Sheldon, RA ;
Arends, IWCE ;
Ten Brink, GJ ;
Dijksman, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :774-781
[53]  
SHELDON RA, 2004, MODERN OXIDATION MET, P83
[54]   Synthesis of polymer-supported TEMPO catalysts and their application in the oxidation of various alcohols [J].
Tanyeli, C ;
Gümüs, A .
TETRAHEDRON LETTERS, 2003, 44 (08) :1639-1642
[55]  
TIDWELL TT, 1990, SYNTHESIS-STUTTGART, P857
[56]   OXIDATION OF ALCOHOLS WITH COPPER(II) SALTS MEDIATED BY NITROXYL RADICALS IMMOBILIZED ON ULTRAFINE SILICA AND FERRITE SURFACE [J].
TSUBOKAWA, N ;
KIMOTO, T ;
ENDO, T .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 101 (01) :45-50
[57]  
Verhoef MJ, 1999, STUD SURF SCI CATAL, V125, P465
[58]   TEMPO-derived task-specific ionic liquids for oxidation of alcohols [J].
Wu, XE ;
Ma, L ;
Ding, MX ;
Gao, LX .
SYNLETT, 2005, (04) :607-610