Copper-catalysed aerobic oxidation of alcohols using fluorous biphasic catalysis

被引:165
作者
Ragagnin, G
Betzemeier, B
Quici, S
Knochel, P
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] CNR, Ctr Sintesi & Stereochim Speciali Sistemi Organ, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
关键词
alcohols oxidation; TEMPO; fluorinated copper ligands; cyclohexanols; fluorous catalysis;
D O I
10.1016/S0040-4020(02)00250-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper(I) catalysed and TEMPO mediated fluorous biphasic oxidation of primary, secondary, allylic and benzylic alcohols with oxygen in the presence of a bipyridine ligand bearing perfluorinated ponytails is described. High chemoselectivities are observed in the oxidation of substituted cyclohexanols (substituted axial cyclohexanols react 6-8 times faster than the corresponding equatorial cyclohexanols). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3985 / 3991
页数:7
相关论文
共 41 条
[31]   Pd(OAc)2-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen [J].
Nishimura, T ;
Onoue, T ;
Ohe, K ;
Uemura, S .
TETRAHEDRON LETTERS, 1998, 39 (33) :6011-6014
[32]   Palladium-catalyzed oxidation of primary and secondary allylic and benzylic alcohols [J].
Peterson, KP ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3185-3189
[33]   Cobalt tetraarylporphyrin-catalysed epoxidation of alkenes by dioxygen and 2-methylpropanal under fluorous biphasic conditions [J].
Pozzi, G ;
Montanari, F ;
Quici, S .
CHEMICAL COMMUNICATIONS, 1997, (01) :69-70
[34]   Efficient aerobic epoxidation of alkenes in perfluorinated solvents catalysed by chiral (salen) Mn complexes [J].
Pozzi, G ;
Cinato, F ;
Montanari, F ;
Quici, S .
CHEMICAL COMMUNICATIONS, 1998, (08) :877-878
[35]   Synthesis of perfluoroalkylated bipyridines - New ligands for oxidation reactions under fluorous triphasic conditions [J].
Quici, S ;
Cavazzini, M ;
Ceragioli, S ;
Montanari, F ;
Pozzi, G .
TETRAHEDRON LETTERS, 1999, 40 (18) :3647-3650
[36]   MECHANISM OF THE OXIDATION OF ALCOHOLS BY 2,2,6,6-TETRAMETHYLPIPERIDINE NITROSONIUM CATION [J].
SEMMELHACK, MF ;
SCHMID, CR ;
CORTES, DA .
TETRAHEDRON LETTERS, 1986, 27 (10) :1119-1122
[37]   NITROXYL-MEDIATED ELECTROOXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES [J].
SEMMELHACK, MF ;
CHOU, CS ;
CORTES, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4492-4494
[38]   New developments in catalytic alcohol oxidations for fine chemicals synthesis [J].
Sheldon, RA ;
Arends, IWCE ;
Dijksman, A .
CATALYSIS TODAY, 2000, 57 (1-2) :157-166
[39]   Synthesis, reactivity, and metal complexes of fluorous triarylphosphines of the formula P(p-C6H4(CH2)3(CF2)n-1CF3)3 (n=6, 8, 10) [J].
Soós, T ;
Bennett, BL ;
Rutherford, D ;
Barthel-Rosa, LP ;
Gladysz, JA .
ORGANOMETALLICS, 2001, 20 (14) :3079-3086
[40]  
ten Brink GJ, 2000, SCIENCE, V287, P1636