Development of a continuous-flow system for catalysis with palladium(O) particles

被引:114
作者
Solodenko, W
Wen, HL
Leue, S
Stuhlmann, F
Sourkouni-Argirusi, G
Jas, G
Schönfeld, H
Kunz, U
Kirschning, A
机构
[1] Leibniz Univ Hannover, Zentrum Organ Chem, D-30167 Hannover, Germany
[2] Chelona GmbH, D-14473 Potsdam, Germany
[3] Tech Univ Clausthal, Inst Chem Verfahrenstech, D-38678 Clausthal Zellerfeld, Germany
关键词
continuous-flow processes; heterogeneous catalysis; hydrogenation; palladium; supported catalysts;
D O I
10.1002/ejoc.200400194
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heterogeneous catalysis for organic synthesis under continuous-flow conditions becomes possible by a new reactor-based approach. Continuous-flow reactors with a monolithic glass/polymer composite interior are loaded with palladium particles by ion exchange followed by reduction. When incorporated into a continuous-flow setup (PASSflow) this reactor allows the transfer-hydrogenation of alkenes, alkynes, nitro-substituted aromatic compounds and benzyl ethers in the flow-through mode. In addition, the activity of the catalysts is well suited to achieve Suzuki, Sonogashira and Heck cross-coupling reactions in the absence of phosphanes or any other ligands, resulting in a greatly simplified purification. As an extension to this concept a bifunctional support was prepared inside the reactor consisting of Pd particles and an ion-exchange group (hydroxide form). In the Suzuki-Miyaura reaction the reactor serves as a base for immobilisation and activation of the boronic acid as boronate and as a catalyst for promoting the C-C coupling reaction under continuous-flow conditions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:3601 / 3610
页数:10
相关论文
共 116 条
[21]  
CAMERON JH, 1999, SOLID STATE ORGANOME, P473
[22]  
Caruso F, 2001, ADV MATER, V13, P11, DOI 10.1002/1521-4095(200101)13:1<11::AID-ADMA11>3.0.CO
[23]  
2-N
[24]   Reduction of conjugate double bonds with trichlorosilane [J].
Chauhan, M ;
Boudjouk, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2000, 78 (11) :1396-1398
[25]   Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes [J].
Choudary, BM ;
Madhi, S ;
Chowdari, NS ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14127-14136
[26]   A new bifunctional catalyst for tandem Heck-asymmetric dihydroxylation of olefins [J].
Choudary, BM ;
Chowdari, NS ;
Jyothi, K ;
Kumar, NS ;
Kantam, ML .
CHEMICAL COMMUNICATIONS, 2002, (06) :586-587
[27]   Polymer-supported catalysis in synthetic organic chemistry [J].
Clapham, B ;
Reger, TS ;
Janda, KD .
TETRAHEDRON, 2001, 57 (22) :4637-4662
[28]   Environmentally friendly catalytic methods [J].
Clark, JH ;
Macquarrie, DJ .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (05) :303-&
[29]   Suzuki-Miyaura cross-coupling with quasi-heterogeneous palladium [J].
Conlon, DA ;
Pipik, B ;
Ferdinand, S ;
LeBlond, CR ;
Sowa, JR ;
Izzo, B ;
Collins, P ;
Ho, GJ ;
Williams, JM ;
Shi, YJ ;
Sun, YK .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :931-935
[30]   Are heterogeneous catalysts precursors to homogeneous catalysts? [J].
Davies, IW ;
Matty, L ;
Hughes, DL ;
Reider, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) :10139-10140