pH-dependent cross-coupling reactions of water-soluble organic halides with organoboron compounds catalyzed by the organometallic aqua complex [(SCS)PdII(H2O)]+ (SCS = C6H3-2,6-(CH2SBut)2)

Organometallics

Volumn 21, Issue 8, 2002, Pages 1674-1678

  Nakai, Hidetaka ^a   Ogo, Seiji ^a   Watanabe, Yoshihito ^a,b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b Myodaiji cho   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; PH EFFECTS; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

CROSS-COUPLING REACTIONS;

ORGANOMETALLICS;

EID: 0013309970     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0109298     Document Type: Article

References (44)

1. (a) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH: Weinheim, Germany, 1998; p 615.
2. (b) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; Wiley: New York, 1997; p 199.
3. (c) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic: Dordrecht, The Netherlands, 1995; p 317.
4. (d) Joó F.; Kathó, A. J. Mol Catal. A 1997, 116, 3-26.
5. (e) Koelle, U. Coord. Chem. Rev. 1994, 135/136, 623-650.
6. (f) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
7. (a) Joó, F.; Kovács, J.; Bényei, A. C.; Nádasdi, L.; Laurenczy, G. Chem. Eur. J. 2001, 7, 193-199.
8. (b) Kovács, J.; Todd, T. D.; Reibenspies, J. H.; Joó, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963-3969.
9. (c) Tin, K.-C.; Wong, N.-B.; Li, R.-X.; Li, Y.-Z.; Hu, J.-Y.; Li, X.-J. J. Mol. Catal. A 1999, 137, 121-125.
10. (d) Joó, F.; Kovács, J.; Bényei, A. C.; Kathó, A. Angew. Chem., Int. Ed. 1998, 37, 969-970.
11. (e) Joó, F.; Nádasdi, L.; Bényei, A. C.; Darensbourg, D. J. J. Organomet. Chem. 1996, 512, 45-50.
12. (a) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523-6526.
13. (b) Hessler, A.; Stelzer, O. J. Org. Chem. 1997, 62, 2362-2369.
14. (c) Genêt, J.-P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
15. (d) Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.
16. (a) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 2001, 20, 4903-4910.
17. (b) Makihara, N.; Ogo, S.; Watanabe, Y. Organometallics 2001, 20, 497-500.
18. (c) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470-5474.
19. (d) Ogo, S.; Buriez, O.; Kerr, J. B.; Fish, R. H. J. Organomet. Chem. 1999, 589, 66-74.
20. (e) Ogo, S.; Chen, H.; Olmstead, M. M.; Fish, R. H. Organometallics 1996, 15, 2009-2013.
21. (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750-3681.
22. (b) Meijer, M. D.; Ronde, N.; Vogt, D.; van Klink, G. P. M.; van Koten, G. Organometallics 2001, 20, 3993-4000.
23. (c) Fidalgo, E. G.; Plasseraud, L.; Süss-Fink, G. J. Mol. Catal. A 1998, 132, 5-12.
24. (d) Jahncke, M.; Meister, G.; Rheinwald, G.; Stoeckli-Evans, H.; Süss-Fink, G. Organometallics 1997, 16, 1137-1143.
25. (a) Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23-41.
26. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
27. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
28. (a) Genêt, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317.
29. (b) Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437-14450.
30. (c) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173.
31. (d) Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
32. Steigman, J.; Sussman, D. J. Am. Chem. Soc. 1967, 89, 6406-6410.
33. Errington, J.; McDonald, W. S.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 2312-2314.
34. 6) have been deposited with the Cambridge Crystallographic Data Center as Supplementary Publication No. CCDC-172019. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB21EZ, U.K. (fax, (+44)1223-336-033; e-mail, deposit@ccdc.cam.ac.uk).
35. 1H NMR signals at pH 10.7 are broadened. This reflects the existence of aqua and hydroxo complexes in rapid equilibrium.
36. 4 acid, sodium salt.
37. Dadci, L.; Elias, H.; Frey, U.; Hörnig, A.; Koelle, U.; Merbach, A. E.; Paulus, H.; Schneider, J. S. Inorg. Chem. 1995, 34, 306-315.
38. -.
39. (a) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064.
40. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884.
41. (c) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287-1290.
42. (d) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531-9538.
43. Brown, R. D.; Buchanan, A. S.; Humffray, A. A. Aust. J. Chem. 1965, 18, 1527-1538.
44. Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034-5037.