Organic-inorganic hybrid materials containing 15-membered azamacrocyclic triolefinic palladium(0) complexes -: Preparation and activity as recoverable catalysts in Suzuki cross-couplings

被引:20
作者
Blanco, Belen
Moreno-Manas, Marcial
Pleixats, Roser [1 ]
Mehdi, Ahmad
Reye, Catherine
机构
[1] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain
[2] Univ Montpellier 2, Lab Chim Mol & Org Solide, UMR 5637, CNRS,Inst Charles Gerhardt, F-34095 Montpellier 5, France
关键词
cross-coupling; macrocycles; palladium supported catalyst; sol-gel processes; recyclable catalyst;
D O I
10.1016/j.molcata.2007.01.026
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis of a palladium complex and a monosilylated monomer derived from 15-membered azatriolefinic macrocycle are described as well as the preparation of the corresponding hybrid organic-inorganic materials, containing a macrocyclic palladium(0) complex covalently anchored to the silica matrix. The materials were obtained by sol-gel process using different routes: post-synthesis treatment on a mesostructured silica, cogelification of a monosilylated precursor and tetraethylorthosilicate. The activity of the different materials as recoverable catalysts in Suzuki cross-couplings is reported and commented. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:204 / 213
页数:10
相关论文
共 54 条
[1]   Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water [J].
Baleizao, C ;
Corma, A ;
García, H ;
Leyva, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) :439-446
[2]   An oxime-carbapalladacycle complex covalently anchored to silica as an active and reusable heterogeneous catalyst for Suzuki cross-coupling in water [J].
Baleizao, C ;
Corma, A ;
García, H ;
Leyva, A .
CHEMICAL COMMUNICATIONS, 2003, (05) :606-607
[3]   Nanoparticulate palladium supported by covalently modified silicas: Synthesis, characterization, and application as catalysts for the Suzuki coupling of aryl halides [J].
Bedford, RB ;
Singh, UG ;
Walton, RI ;
Williams, RT ;
Davis, SA .
CHEMISTRY OF MATERIALS, 2005, 17 (04) :701-707
[4]   Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction? [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Pike, KJ ;
Wimperis, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) :173-181
[5]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[6]   Preparation of a hybrid organic-inorganic material containing macrocyclic triolefinic 15-membered palladium(0) complex -: Catalytic activity in Suzuki cross-coupling and butadiene telomerization reactions [J].
Blanco, B ;
Brissart, M ;
Moreno-Mañas, M ;
Pleixats, R ;
Mehdi, A ;
Reyé, C ;
Bouquillon, S ;
Hénin, F ;
Muzart, J .
APPLIED CATALYSIS A-GENERAL, 2006, 297 (02) :117-124
[7]   Preparation of nitrogen-containing 25-membered pentaolefinic macrocycles:: (E,E,E,E,E)-1,6,11,16,21-penta(arylsulfonyl)-1,6,11,16,21-pentaazacyclopentacosa-3,8,13,18,23-pentaenes [J].
Blanco, B ;
Christensen, J ;
Maurel, I ;
Pleixats, R ;
Serra, A ;
Pla-Quintana, A ;
Roglans, A ;
Benet-Buchholz, J .
SYNTHESIS-STUTTGART, 2005, (03) :374-380
[8]   A macrocyclic triolefinic palladium(0) complex covalently anchored to a mesostructured silica as active and reusable catalyst for Suzuki cross-coupling reactions [J].
Blanco, B ;
Mehdi, A ;
Moreno-Mañas, M ;
Pleixats, R ;
Reyé, C .
TETRAHEDRON LETTERS, 2004, 45 (48) :8789-8791
[9]   The [(E,E,E)-1,6,11-tris(p-toluenesulfonyl)-1,6,11-triazacyclopentadeca-3,18,13-triene]Pd(0) complex in the hydroarylation of alkynes in ionic liquids.: An approach to quinolines [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Moreno-Mañas, M ;
Vallribera, A .
TETRAHEDRON LETTERS, 2002, 43 (32) :5537-5540
[10]  
Cerezo S, 1999, RAPID COMMUN MASS SP, V13, P2359, DOI 10.1002/(SICI)1097-0231(19991215)13:23<2359::AID-RCM799>3.0.CO