Silica-supported TEMPO catalysts: Synthesis and application in the Anelli oxidation of alcohols

被引:210
作者
Fey, T
Fischer, H
Bachmann, S
Albert, K
Bolm, C
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
[2] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
关键词
D O I
10.1021/jo010535q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The application of silica-supported TEMPO as a recyclable catalyst in the Anelli oxidation of alcohols is reported. The catalyst is easily obtained in a one-step reductive amination procedure starting from a commercially available aminopropyl-functionalized silica. Details of the synthesis of the supported catalyst and its analysis by MAS NMR are presented. Various alcohol oxidations according to the Anelli protocol have been carried out and the stability of the applied silica-supported TEMPO has been studied.
引用
收藏
页码:8154 / 8159
页数:6
相关论文
共 84 条
[1]   APPLICATION OF FUNCTIONALIZED POLYMERS IN ORGANIC-SYNTHESIS [J].
AKELAH, A ;
SHERRINGTON, DC .
CHEMICAL REVIEWS, 1981, 81 (06) :557-587
[2]   ADSORPTION OF RANDOM COPOLYMERS ON SILICA - EPR SPECTROSCOPY STUDY [J].
AMIEL, C ;
SEBILLE, B ;
HOMMEL, H ;
LEGRAND, AP .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 1994, 165 (01) :236-243
[3]  
ANELLI PL, 1987, J ORG CHEM, V52, P2559
[4]   Copper-catalyzed aerobic oxidation of alcohols under fluorous biphasic conditions [J].
Betzemeier, B ;
Cavazzini, M ;
Quici, S ;
Knochel, P .
TETRAHEDRON LETTERS, 2000, 41 (22) :4343-4346
[5]  
Bhalay G, 2000, SYNLETT, P1846
[6]   Oxoammonium salts. 6. 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis [J].
Bobbitt, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9367-9374
[7]  
BOBBITT JM, 1988, HETEROCYCLES, V27, P509
[8]  
Bobbitt JM, 1999, CHEM ENG NEWS, V77, P6
[9]   TEMPO oxidations with a silica-supported catalyst [J].
Bolm, C ;
Fey, T .
CHEMICAL COMMUNICATIONS, 1999, (18) :1795-1796
[10]   Catalytic synthesis of aldehydes and ketones under mild conditions using TEMPO/Oxone [J].
Bolm, C ;
Magnus, AS ;
Hildebrand, JP .
ORGANIC LETTERS, 2000, 2 (08) :1173-1175