Highly efficient C-H insertion reactions of hydrogen peroxide catalyzed by homogeneous and heterogeneous methyltrioxorhenium systems in ionic liquids

被引:51
作者
Bianchini, G
Crucianelli, M
De Angelis, F
Neri, V
Saladino, R
机构
[1] Univ Tuscia, Dipartimento ABAC, INFM, I-01100 Viterbo, Italy
[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Coppito, AQ, Italy
关键词
C-H insertion reaction; heterogeneous catalysis; hydrogen peroxide; methyltrioxorhenium; ionic liquid;
D O I
10.1016/j.tetlet.2005.02.056
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and efficient C-H insertion reaction of environment friendly H2O2 into representative hydrocarbon derivatives by homogeneous methyltrioxorhenium (MTO), heterogeneous poly(4-vinylpyridine)/methyltrioxorhenium (PVP/MTO) and microencapsulated polystyrene/methyltrioxorhenium (PS/MTO) systems in ionic liquids, is described. In some cases a higher activity was observed if compared with the same reaction in molecular solvents. The heterogeneous catalysts are stable systems under the reaction conditions and can be recycled for more transformations. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2427 / 2432
页数:6
相关论文
共 48 条
[1]   OXIDATION OF METHOXYBENZENES TO P-BENZOQUINONES CATALYZED BY METHYLTRIOXORHENIUM(VII) [J].
ADAM, W ;
HERRMANN, WA ;
SAHAMOLLER, CR ;
SHIMIZU, M .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 97 (01) :15-20
[2]   Homogeneous catalysis - Toward greener chemistry [J].
Baker, RT ;
Tumas, W .
SCIENCE, 1999, 284 (5419) :1477-1479
[3]   CH3ReO3/H2O2 in room temperature ionic liquids:: an homogeneous recyclable catalytic system for the Baeyer-Villiger reaction [J].
Bernini, R ;
Coratti, A ;
Fabrizi, G ;
Goggiamani, A .
TETRAHEDRON LETTERS, 2003, 44 (50) :8991-8994
[4]   A novel catalyzed C-H insertion reactions of hydrogen peroxide by poly(4-vinylpyridine)/methyltrioxorhenium systems [J].
Bianchini, G ;
Crucianelli, M ;
De Angelis, F ;
Neri, V ;
Saladino, R .
TETRAHEDRON LETTERS, 2004, 45 (11) :2351-2353
[5]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[6]  
Chauvin Y, 1995, ANGEW CHEM INT EDIT, V34, P2698
[7]   Ionic liquid (molten salt) phase organometallic catalysis [J].
Dupont, J ;
de Souza, RF ;
Suarez, PAZ .
CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691
[8]   Diels-Alder reactions in ionic liquids - A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures [J].
Earle, MJ ;
McCormac, PB ;
Seddon, KR .
GREEN CHEMISTRY, 1999, 1 (01) :23-25
[9]   Ionic liquids - An overview [J].
Forsyth, SA ;
Pringle, JM ;
MacFarlane, DR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (02) :113-119
[10]   MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .122. METHYLTRIOXORHENIUM(VII) AS CATALYST FOR EPOXIDATIONS - STRUCTURE OF THE ACTIVE SPECIES AND MECHANISM OF CATALYSIS [J].
HERRMANN, WA ;
FISCHER, RW ;
SCHERER, W ;
RAUCH, MU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (08) :1157-1160