A fluorous phase approach to rhodium-catalyzed carbenoid reactions with diazoacetates

被引:32
作者
Endres, A [1 ]
Maas, G [1 ]
机构
[1] Univ Ulm, Abt Organ Chem 1, D-89081 Ulm, Germany
关键词
cyclopropanes; diazo compounds; perfluoroalkyl compounds; rhodium and compounds;
D O I
10.1016/S0040-4039(99)01332-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclopropanation of alkenes with methyl diazoacetate in dichloromethane was catalyzed by rhodium(II) carboxylates containing a perfluoralkyl chain (Rh2L4, L = OOCC7F15 and OOC-C6H4-4-C6F13) The catalysts could be extracted into perfluoro(methylcyclohexane) and were reused several times without significant loss of activity. The same catalysts were used to achieve carbene transfer to toluene in the solvent system toluene-perfluoro(methylcyclohexane) at 60 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6365 / 6368
页数:4
相关论文
共 26 条
[1]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[2]   TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .1. CYCLOPROPANATION OF DOUBLE-BONDS [J].
ANCIAUX, AJ ;
HUBERT, AJ ;
NOELS, AF ;
PETINIOT, N ;
TEYSSIE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) :695-702
[3]   TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .2. ADDITION TO AROMATIC-MOLECULES - CATALYSIS OF BUCHNER SYNTHESIS OF CYCLOHEPTATRIENES [J].
ANCIAUX, AJ ;
DEMONCEAU, A ;
NOELS, AF ;
HUBERT, AJ ;
WARIN, R ;
TEYSSIE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (05) :873-876
[4]   CATALYTIC CYCLOPROPANATION WITH TRANSITION-METAL SALTS OF SOLUBLE POLYETHYLENE CARBOXYLATES [J].
BERGBREITER, DE ;
MORVANT, M ;
CHEN, B .
TETRAHEDRON LETTERS, 1991, 32 (24) :2731-2734
[5]   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
[6]   Wacker oxidation of alkenes using a fluorous biphasic system. A mild preparation of polyfunctional ketones [J].
Betzemeier, B ;
Lhermitte, F ;
Knochel, P .
TETRAHEDRON LETTERS, 1998, 39 (37) :6667-6670
[7]   EXCITING RESULTS FROM THE FIELD OF HOMOGENEOUS 2-PHASE CATALYSIS [J].
CORNILS, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1575-1577
[8]  
CORNILS B, 1995, ANGEW CHEM, V107, P1709
[9]  
Curran DP, 1998, ANGEW CHEM INT EDIT, V37, P1175, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1174::AID-ANIE1174>3.0.CO
[10]  
2-P