A recyclable nanosize aminoarenethiolato copper(I) catalyst for C-C coupling reactions

Journal of Organometallic Chemistry

Volumn 689, Issue 23, 2004, Pages 3813-3819

  Arink, Anne M ^a   Van De Coevering, Rob ^a   Wieczorek, Birgit ^a   Firet, Judith ^a   Jastrzebski, Johann T B H ^a   Gebbink, Robertus J M Klein ^a   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Aminoarenethiolate; Carbosilane dendrimer; Catalysis; Copper catalyst; Nanofiltration; Recycling

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; CHEMICAL BONDS; DENDRIMERS; HYDROLYSIS; NANOFILTRATION; NANOSTRUCTURED MATERIALS; ORGANIC SOLVENTS; OXIDATION; REACTION KINETICS; RECYCLING; SILANES;

AMINOARENETHIOLATE; CARBOSILANE DENDRIMERS; COPPER CATALYSTS; FAST ATOM BOMBARDMENT (FAB);

COPPER COMPOUNDS;

EID: 19344367244     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.07.023     Document Type: Article

References (29)

1. R. Kreiter, A.W. Kleij, R.J.M. Klein Gebbink, and G. van Koten Top. Curr. Chem. 217 2001 163
2. R. van Heerbeek, P.C.J. Kamer, P.W.N.M. van Leeuwen, and J.N.H. Reek Chem. Rev. 102 2002 3717
3. H.P. Dijkstra, G.P.M. van Klink, and G. van Koten Acc. Chem. Res. 35 2002 798
4. I.F.J. Vankelecom Chem. Rev. 102 2002 3779
5. C.C. Mak, and H.-F. Chow Macromolecules 30 1997 1228
6. M. van Klaveren, F. Lambert, J.F.M. Eijkelkamp, D.M. Grove, and G. van Koten Tetrahedron Lett. 35 1994 6135
7. Q.L. Zhou, and A. Pfaltz Tetrahedron 50 1994 4467
8. M. Spescha, and G. Rihs Helv. Chim. Acta 76 1993 1219
9. D. Seebach, G. Jaeschke, A. Pichota, and L. Audergon Helv. Chim. Acta 80 1997 2515
10. A. Haubrich, M. van Klaveren, G. van Koten, G. Handke, and N. Krause J. Org. Chem. 58 1993 5849
11. G.J. Meuzelaar, A.S.E. Karlström, M. van Klaveren, E.S.M. Persson, A. del Villar, G. van Koten, and J.-E. Bäckvall Tetrahedron 56 2000 2895
12. M. van Klaveren, E.S.M. Persson, A. del Villar, D.M. Grove, J.-E. Bäckvall, and G. van Koten Tetrahedron Lett. 36 1995 3059
13. F. Lambert, D.M. Knotter, M.D. Janssen, M. van Klaveren, J. Boersma, and G. van Koten Tetrahedron Lett. 2 1991 1097
14. A.M. Arink, T.W. Braam, R. Keeris, J.T.B.H. Jastrzebski, C. Benhaim, S. Rosset, A. Alexakis, and G. van Koten Org. Lett. 6 2004 1959
15. D.M. Knotter, M.D. Janssen, D.M. Grove, W.J.J. Smeets, E. Horn, A.L. Spek, and G. van Koten Inorg. Chem. 30 1991 4361
16. D.M. Knotter, G. van Koten, H.L. van Maanen, D.M. Grove, and A.L. Spek Angew. Chem. Int. Ed. Engl. 28 1989 341
17. N.J. Hovestad, J.T.B.H. Jastrzebski, G. van Koten, S.A.F. Bon, C. Waterson, and D.M. Haddleton Polym. Prep. 1999 393
18. N.J. Hovestad, E.B. Eggeling, H.J. Heidbüchel, J.T.B.H. Jastrzebski, U. Kragl, W. Keim, D. Vogt, and G. van Koten Angew. Chem. Int. Ed. 38 1999 1655
19. A.W. Kleij, R.A. Gossage, R.J.M. Klein Gebbink, N. Brinkmann, E.J. Reijers, U. Kragl, M. Lutz, A.L. Spek, and G. van Koten J. Am. Chem. Soc. 122 2000 12112
20. A.W. Kleij, H. Kleijn, J.T.B.H. Jastrzebski, W.J.J. Smeets, A.L. Spek, and G. van Koten Organometallics 18 1999 268
21. Excess of lithiating reagent had also been required, when fluorous tails were attached to the para-position: H. Kleijn, E. Rijnberg, J.T.B.H. Jastrzebski, and G. van Koten Org. Lett. 1 1999 853
22. Commercially available dialysis membranes were employed (benzoylated cellulose, Sigma)
23. Dialysis specifications were given for compounds in aqueous solutions
24. C.B. Gorman, B.L. Parkhurst, W.Y. Su, and K.-Y. Chen J. Am. Chem. Soc. 119 1997 1141
25. C.B. Gorman, J.C. Smith, M.W. Hager, B.L. Parkhurst, H. Sierzputowska-Gracz, and C.A. Haney J. Am. Chem. Soc. 121 1999 9958
26. C.B. Gorman, W.Y. Su, H. Jiang, C.M. Watson, and P. Boyle Chem. Commun. 1999 877
27. R. Wang, and Z. Zheng J. Am. Chem. Soc. 121 1999 3549
28. For molecular modeling the Spartan 5.1.1. (SGI) program was used with MMFF94 as a force field. The molecular volumes where determined with the same program, using the smallest spherical shape to fit the molecule. In this way solvent effects are not included
29. M. Enomoto, and T. Aida J. Am. Chem. Soc. 121 1999 874