Conjugate addition to diethyl azodicarboxylate under organic-perfluorinated biphasic homogeneous catalysis by nickel(II) species

被引:36
作者
Meseguer, M [1 ]
Moreno-Mañas, M [1 ]
Vallribera, A [1 ]
机构
[1] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain
关键词
Michael reactions; nickel(II); catalysis; amination;
D O I
10.1016/S0040-4039(00)00549-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The nickel(II) complex of the Schiff base of salicylaldehyde and 4-perfluorodecylaniline catalyzes the conjugate addition of beta-diketones to electron-deficient substrates. Electrophilic amination with azodicarboxylate affords quaternary centers. The catalyst is recovered in solution and reutilized. Isolation of reaction products is very simple and does not require chromatography. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4093 / 4095
页数:3
相关论文
共 27 条
[1]   Fluoroacrylate-bound fluorous-phase soluble hydrogenation catalysts [J].
Bergbreiter, DE ;
Franchina, JG ;
Case, BL .
ORGANIC LETTERS, 2000, 2 (03) :393-395
[2]   Palladium-catalyzed cross-coupling of organozinc bromides with aryl iodides in perfluorinated solvents [J].
Betzemeier, B ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2623-2624
[3]  
Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259
[4]   Nickel(II)-catalyzed Michael additions.: Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4-benzyloxazolidin-2-one [J].
Clariana, J ;
Gálvez, N ;
Marchi, C ;
Mañas, MM ;
Vallribera, A ;
Molins, E .
TETRAHEDRON, 1999, 55 (23) :7331-7344
[5]   Fluorous biphase systems - The new phase-separation and immobilization technique [J].
Cornils, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (19) :2057-2059
[6]   Copper(I) complexes mediated cyclization reaction of unsaturated ester under fluoro biphasic procedure [J].
De Campo, F ;
Lastécouères, D ;
Vincent, JM ;
Verlhac, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4969-4971
[7]   Fluorous phase separation techniques in catalysis [J].
de Wolf, E ;
van Koten, G ;
Deelman, BJ .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) :37-41
[8]   A fluorous phase approach to rhodium-catalyzed carbenoid reactions with diazoacetates [J].
Endres, A ;
Maas, G .
TETRAHEDRON LETTERS, 1999, 40 (35) :6365-6368
[9]  
Fish RH, 1999, CHEM-EUR J, V5, P1677, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1677::AID-CHEM1677>3.3.CO
[10]  
2-O