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
[91]  
2-1
[92]   Suzuki and Heck reactions catalyzed by preformed palladium clusters and palladium/nickel bimetallic clusters [J].
Reetz, MT ;
Breinbauer, R ;
Wanninger, K .
TETRAHEDRON LETTERS, 1996, 37 (26) :4499-4502
[93]  
Reetz MT, 2000, ANGEW CHEM INT EDIT, V39, P165, DOI 10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO
[94]  
2-B
[95]  
REETZ MT, 1996, TETRAHEDRON LETT, P1921
[96]   PHOTOCHEMICAL REACTIONS OF CHLOROBENZENE DERIVATIVES IN BENZENE [J].
ROBINSON, GE ;
VERNON, JM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (20) :3363-&
[97]   Reduced transition metal colloids: A novel family of reusable catalysts? [J].
Roucoux, A ;
Schulz, J ;
Patin, H .
CHEMICAL REVIEWS, 2002, 102 (10) :3757-3778
[98]   Preparation and structural characterization of polymer-supported methylrhenium trioxide systems as efficient and selective catalysts for the epoxidation of olefins [J].
Saladino, R ;
Neri, V ;
Pelliccia, AR ;
Caminiti, R ;
Sadun, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1323-1332
[99]   Photophysical studies of substituted 1,2-diarylethenes: twisted intramolecular charge transfer fluorescence in dimethoxycyano-substituted 1,2-diarylethene [J].
Singh, AK ;
Kanvah, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (03) :395-401
[100]   MECHANISTIC STUDIES OF THE SUZUKI CROSS-COUPLING REACTION [J].
SMITH, GB ;
DEZENY, GC ;
HUGHES, DL ;
KING, AO ;
VERHOEVEN, TR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8151-8156