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
[31]   Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts [J].
Einhorn, J ;
Einhorn, C ;
Ratajczak, F ;
Pierre, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7452-7454
[32]   Facile preparation of nucleoside-5′-carboxylic acids [J].
Epp, JB ;
Widlanski, TS .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :293-295
[33]   MECHANISM OF OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS BY OXOPIPERIDINIUM SALTS [J].
GOLUBEV, VA ;
BORISLAVSKII, VN ;
ALEKSANDROV, AL .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1977, 26 (09) :1874-1881
[34]   METHOD FOR DETERMINING THE SPATIAL-DISTRIBUTION OF SPIN-LABELED ORGANIC-LIGANDS COVALENTLY BOUND TO A NONCRYSTALLINE SURFACE - DIPOLAR CONTRIBUTION TO NITROXIDE EPR-SPECTRUM [J].
HALL, LD ;
WATERTON, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) :3697-3698
[35]  
Hallman K, 2001, ADV SYNTH CATAL, V343, P260, DOI 10.1002/1615-4169(20010330)343:3<260::AID-ADSC260>3.3.CO
[36]  
2-#
[37]   Multiple bonds between transition metals and main-group elements Part 175 - The selective catalytic oxidation of terminal alcohols: a novel four-component system with MTO as catalyst [J].
Herrmann, WA ;
Zoller, JP ;
Fischer, RW .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 579 (1-2) :404-407
[38]   INDIRECT ELECTROOXIDATION OF ALCOHOLS BY A DOUBLE MEDIATORY SYSTEM WITH 2 REDOX COUPLES OF [R2N(+)=O]/R2NO. AND [BR. OR BR+]/BR- IN AN ORGANIC AQUEOUS 2-PHASE SOLUTION [J].
INOKUCHI, T ;
MATSUMOTO, S ;
TORII, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2416-2421
[39]   A SELECTIVE AND EFFICIENT METHOD FOR ALCOHOL OXIDATIONS MEDIATED BY N-OXOAMMONIUM SALTS IN COMBINATION WITH SODIUM BROMITE [J].
INOKUCHI, T ;
MATSUMOTO, S ;
NISHIYAMA, T ;
TORII, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :462-466
[40]   Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation [J].
Jurczak, J ;
Gryko, D ;
Kobrzycka, E ;
Gruza, H ;
Prokopowicz, P .
TETRAHEDRON, 1998, 54 (22) :6051-6064