Hydrotrispyrazolylborate-copper complexes as catalysts for the styrene cyclopropanation reaction with ethyl diazoacetate under homogeneous and heterogeneous conditions

被引:5
作者
Caballero, Ana [1 ]
Sabater, Mariano [1 ]
Esther Morilla, M. [1 ]
Carmen Nicasio, M. [1 ]
Belderrain, Tomas R. [1 ]
Mar Diaz-Requejo, M. [1 ]
Perez, Pedro J. [1 ]
机构
[1] Univ Huelva, Dept Quim & Ciencia Mat, Lab Catalisis Homogenea, CSIC,Unidad Asociada, Huelva 21007, Spain
关键词
Hydrotrispyrazolylborate; Copper; Styrene cyclopropanation; Diastereoselectivity; CIS; OLEFINS;
D O I
10.1016/j.ica.2009.05.027
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of complexes of general formulae Tp(x)Cu have been employed as the catalyst for the styrene cyclopropanation reaction with ethyl diazoacetate, both under homogeneous and heterogeneous conditions. Several solid supports have been tested, with silica gel being the most convenient for this transformation. A comparison of the results obtained under both conditions has shown that the catalytic pocket is affected by the support. (C) 2009 Elsevier B. V. All rights reserved.
引用
收藏
页码:4599 / 4602
页数:4
相关论文
共 12 条
[1]   Metal-Catalyzed Olefin Cyclopropanation with Ethyl Diazoacetate: Control of the Diastereoselectivity [J].
Caballero, Ana ;
Prieto, Auxiliadora ;
Mar Diaz-Requejo, M. ;
Perez, Pedro J. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (09) :1137-1144
[2]   From homogeneous to heterogeneous catalysis:: Novel anchoring of polypyrazolylborate copper(I) complexes on silica gel through classical and nonclassical hydrogen bonds.: Use as catalysts of the olefin cyclopropanation reaction [J].
Díaz-Requejo, MM ;
Belderrain, TR ;
Nicasio, MC ;
Pérez, PJ .
ORGANOMETALLICS, 2000, 19 (03) :285-289
[3]   Copper(I)-homoscorpionate catalysts for the preferential, kinetically controlled cis cyclopropanation of α-olefins with ethyl diazoacetate [J].
Díaz-Requejo, MM ;
Caballero, A ;
Belderraín, TR ;
Nicasio, MC ;
Trofimenko, S ;
Pérez, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :978-983
[4]   BpCu-catalyzed cyclopropanation of olefins: A simple system that operates under homogeneous and heterogeneous conditions (Bp=dihydridobis(pyrazolyl)borate) [J].
Diaz-Requejo, MM ;
Nicasio, MC ;
Perez, PJ .
ORGANOMETALLICS, 1998, 17 (14) :3051-3057
[5]   Unprecedented highly cis-diastereoselective olefin cyclopropanation using copper homoscorpionate catalysts [J].
Díaz-Requejo, MM ;
Belderraín, TR ;
Trofimenko, S ;
Pérez, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :3167-3168
[6]  
Doyle M.P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds
[7]  
DOYLE MP, 1995, COMPREHENSIVE ORGANO, V12, P421
[8]   Stereoselective cyclopropanation reactions [J].
Lebel, H ;
Marcoux, JF ;
Molinaro, C ;
Charette, AB .
CHEMICAL REVIEWS, 2003, 103 (04) :977-1050
[9]   Gold-catalyzed olefin cyclopropanation [J].
Prieto, Auxiliadora ;
Fructos, Manuel R. ;
Mar Diaz-Requejo, M. ;
Perez, Pedro J. ;
Perez-Galan, Patricia ;
Delpont, Nicolas ;
Echavarren, Antonio M. .
TETRAHEDRON, 2009, 65 (09) :1790-1793
[10]   Enhancement of cyclopropanation chemistry in the silver-catalyzed reactions of aryldiazoacetates [J].
Thompson, Janelle L. ;
Davies, Huw M. L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) :6090-+