Comparison of palladium carbene and palladium phosphine catalysts for catalytic coupling reactions of aryl halides

Journal of Molecular Catalysis A: Chemical

Volumn 214, Issue 2, 2004, Pages 231-239

  Frisch, Anja C ^a   Zapf, Alexander ^a   Briel, Oliver ^b   Kayser, Bernd ^b   Shaikh, Nadim ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UMICORE AG AND CO KG   (Germany)

Author keywords

Aryl halides; Carbene ligands; Homogeneous catalysis; Palladium; Phosphine ligands

Indexed keywords

AMINATION; CATALYSTS; CHEMICAL BONDS; PALLADIUM COMPOUNDS;

BOND FORMING REACTIONS; CATALYTIC PERFORMANCE; COUPLING REACTIONS;

CATALYSIS;

CARBENOID; HALIDE; PALLADIUM CARBENE; PALLADIUM COMPLEX; PALLDIUM PHOSPHINE; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BUTCHWALD HARTWIG AMINATION REACTION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL INDUSTRY; CHEMICAL REACTION; KUMADA REACTION; SUZUKI REACTION;

EID: 2442490921     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2003.12.035     Document Type: Article

References (82)

1. T. Henkel, R.M. Brunne, H. Müller, F. Reichel, Angew. Chem. 111 (1999) 688; Angew. Chem. Int. Ed. 38 (1999) 643.
2. T. Henkel, R.M. Brunne, H. Müller, F. Reichel, Angew. Chem. 111 (1999) 688; Angew. Chem. Int. Ed. 38 (1999) 643.
3. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457
4. A. Suzuki, in: F. Diederich, P.J. Stang (Eds.), Metal-catalyzed Cross-coupling Reactions, Wiley-VCH, Weinheim, 1997, p. 49.
5. A. Suzuki, in: E.-i. Negishi (Ed.), Organopalladium Chemistry for Organic Synthesis, vol. 1, Wiley-Interscience, New York, 2002, p. 249.
6. E.-i. Negishi (Ed.), Organopalladium Chemistry for Organic Synthesis, vol. 1, Wiley-Interscience, New York, 2002, pp. 1123-1315.
7. Whitcombe N.J., Hii K.K., Gibson S.E. Tetrahedron. 57:2001;7449
8. L. Anastasia, E.-i. Negishi, in: E.-i. Negishi (Ed.), Organopalladium Chemistry for Organic Synthesis, vol. 1, Wiley-Interscience, New York, 2002, p. 311.
9. J.F. Hartwig, in: E.-i. Negishi (Ed.), Organopalladium Chemistry for Organic Synthesis, vol. 1, Wiley-Interscience, New York, 2002, p. 1051.
10. Beller M., Zapf A., Mägerlein W. Chem. Eng. Technol. 24:2001;575
11. Zapf A., Beller M. Top. Catal. 19:2002;101
12. de Vries J.G. Can. J. Chem. 79:2001;1086
13. R.B. Bedford, C.S.J. Cazin, S.L. Hazelwood (née Welch), Angew. Chem. 114 (2002) 4294; Angew. Chem. Int. Ed. 41 (2002) 4120.
14. R.B. Bedford, C.S.J. Cazin, S.L. Hazelwood (née Welch), Angew. Chem. 114 (2002) 4294; Angew. Chem. Int. Ed. 41 (2002) 4120.
15. R. Jackstell, M. Gómez Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 114 (2002) 1028; Angew. Chem. Int. Ed. 41 (2002) 986.
16. R. Jackstell, M. Gómez Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 114 (2002) 1028; Angew. Chem. Int. Ed. 41 (2002) 986.
17. Loch J.A., Albrecht M., Peris E., Mata J., Faller J.W., Crabtree R.H. Organometallics. 21:2002;700
18. Feuerstein M., Doucet H., Santelli M. Tetrahedron Lett. 42:2001;6667
19. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 112 (2000) 4315; Angew. Chem. Int. Ed. 39 (2000) 4153.
20. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 112 (2000) 4315; Angew. Chem. Int. Ed. 39 (2000) 4153.
21. Zapf A., Beller M. Chem. Eur. J. 6:2000;1830
22. Littke A.F., Dai C., Fu G.C. J. Am. Chem. Soc. 122:2000;4020
23. Bedford R.B., Draper S.M., Scully P.N., Welch S.L. New J. Chem. 2:2000;745
24. Böhm V.P.W., Herrmann W.A. Chem. Eur. J. 6:2000;1017
25. Fox J.M., Huang X., Chieffi A., Buchwald S.L. J. Am. Chem. Soc. 122:2000;1360
26. Kawatsura M., Hartwig J.F. J. Am. Chem. Soc. 121:1999;1473
27. J.P. Wolfe, S.L. Buchwald, Angew. Chem. 111 (1999) 2570; Angew. Chem. Int. Ed. 38 (1999) 2413.
28. J.P. Wolfe, S.L. Buchwald, Angew. Chem. 111 (1999) 2570; Angew. Chem. Int. Ed. 38 (1999) 2413.
29. Wolfe J.P., Singer R.A., Yang B.H., Buchwald S.L. J. Am. Chem. Soc. 121:1999;9550
30. Ohff M., Ohff A., van der Boom M.E., Milstein D. J. Am. Chem. Soc. 119:1997;11687
31. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, G.R.J. Artus, Angew. Chem. 107 (1995) 2602; Angew. Chem. Int. Ed. Engl. 34 (1995) 2371.
32. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, G.R.J. Artus, Angew. Chem. 107 (1995) 2602; Angew. Chem. Int. Ed. Engl. 34 (1995) 2371.
33. A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. (2004) 38.
34. Köhler K., Djakovitch L. Cat. Today. 66:2001;105
35. Herrmann W.A., Öfele K., von Preysing D., Schneider S.K. J. Organomet. Chem. 687:2003;229
36. C.W.K. Gstöttmayr, V.P.W. Böhm, E. Herdtweck, M. Grosche, W.A. Herrmann, Angew. Chem. 114 (2002) 1421; Angew. Chem. Int. Ed. Engl. 34 (1995) 1348.
37. C.W.K. Gstöttmayr, V.P.W. Böhm, E. Herdtweck, M. Grosche, W.A. Herrmann, Angew. Chem. 114 (2002) 1421; Angew. Chem. Int. Ed. Engl. 34 (1995) 1348.
38. Hillier A.C., Grasa G.A., Viciu M.S., Lee H.M., Yang C., Nolan S.P. J. Organomet. Chem. 653:2002;69
39. Ma Y., Song C., Jiang W., Wu Q., Wang Y., Liu X., Andrus M.B. Org. Lett. 5:2003;3317
40. Stauffer S.R., Lee S., Stambuli J.P., Hauck S.I., Hartwig J.F. Org. Lett. 2:2000;1423
41. M. Gómez Andreu, A. Zapf, M. Beller, Chem. Commun. (2000) 2475.
42. Dai C., Fu G.C. J. Am. Chem. Soc. 123:2001;2719
43. P. Stambuli, R. Kuwano, J.F. Hartwig, Angew. Chem. 114 (2002) 4940; Angew. Chem. Int. Ed. 41 (2002) 4746.
44. P. Stambuli, R. Kuwano, J.F. Hartwig, Angew. Chem. 114 (2002) 4940; Angew. Chem. Int. Ed. 41 (2002) 4746.
45. Zim D., Buchwald S.L. Org. Lett. 5:2003;2413
46. Li G.Y. J. Org. Chem. 67:2002;3643
47. A. Schnyder, A.F. Indolese, M. Studer, H.-U. Blaser, Angew. Chem. 114 (2002) 3820; Angew. Chem. Int. Ed. 41 (2002) 3668.
48. A. Schnyder, A.F. Indolese, M. Studer, H.-U. Blaser, Angew. Chem. 114 (2002) 3820; Angew. Chem. Int. Ed. 41 (2002) 3668.
49. Selvakumar K., Zapf A., Spannenberg A., Beller M. Chem. Eur. J. 8:2002;3901
50. Selvakumar K., Zapf A., Beller M. Org. Lett. 4:2002;3031
51. Jackstell R., Frisch A., Beller M., Röttger D., Malaun M., Bildstein B. J. Mol. Catal. 185:2002;105
52. Goa K.L., Wagstaff A.J. Drugs. 51:1996;820
53. E. Mutschler, Arzneimittelwirkungen, 5th ed., Wissenschaftliche Verlagsgesellschaft GmbH, Stuttgart, 1986.
54. Blaser H.-U., Indolese A.F., Schnyder A. Curr. Sci. 78:2000;1336
55. Yin J., Buchwald S.L. J. Am. Chem. Soc. 122:2000;12051
56. E. Poetsch, Kontakte (1988) 15.
57. A.F. Littke, G.C. Fu, Angew. Chem. 114 (2002) 4350; Angew. Chem. Int. Ed. 41 (2002) 4176.
58. A.F. Littke, G.C. Fu, Angew. Chem. 114 (2002) 4350; Angew. Chem. Int. Ed. 41 (2002) 4176.
59. Grasa G.A., Viciu M.S., Huang J., Zhang C., Trudell M.L., Nolan S.P. Organometallics. 21:2002;2866
60. Viciu M.S., Germaneau R.F., Navarro-Fernandez O., Stevens E.D., Nolan S.P. Organometallics. 21:2002;5470
61. Tamao K., Sumitani K., Kumada M. J. Am. Chem. Soc. 94:1972;4374
62. R.J.P. Corriu, J.P. Masse, J. Chem. Soc. Chem. Commun. (1972) 144.
63. Huang J., Nolan S.P. J. Am. Chem. Soc. 121:1999;9889
64. Riermeier T.H., Zapf A., Beller M. Top. Catal. 4:1997;301
65. M. Beller, Angew. Chem. 107 (1995) 1436; Angew. Chem. Int. Ed. Engl. 34 (1995) 1316.
66. M. Beller, Angew. Chem. 107 (1995) 1436; Angew. Chem. Int. Ed. Engl. 34 (1995) 1316.
67. van Leeuwen P.W.N.M., Kamer P.C.J., Reek J.N.H., Dierkes R. Chem. Rev. 100:2000;2741
68. Hopper M.W., Utsunomiya M., Hartwig J.F. J. Org. Chem. 68:2003;2961
69. Kuwano R., Utsunomiya M., Hartwig J.F. J. Org. Chem. 67:2002;6479
70. Kataoka N., Shelby Q., Stambuli J.P., Hartwig J.F. J. Org. Chem. 67:2002;5553
71. Ali M.H., Buchwald S.L. J. Org. Chem. 66:2001;2560
72. Zhang X.-X., Sadighi J.P., Mackewitz T.W., Buchwald S.L. J. Am. Chem. Soc. 122:2000;7606
73. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L. J. Org. Chem. 65:2000;1158
74. Wolfe J.P., Wagaw S., Marcoux J.-F., Buchwald S.L. Acc. Chem. Res. 31:1998;805
75. J.F. Hartwig, Angew. Chem. 110 (1998) 2154; Angew. Chem. Int. Ed. 37 (1998) 2047.
76. J.F. Hartwig, Angew. Chem. 110 (1998) 2154; Angew. Chem. Int. Ed. 37 (1998) 2047.
77. Marcoux J.-F., Wagaw S., Buchwald S.L. J. Org. Chem. 62:1997;1568
78. J.F. Hartwig, Synlett (1997) 329.
79. A.S. Guram, R.A. Rennels, S.L. Buchwald, Angew. Chem. 107 (1995) 1456; Angew. Chem. Int. Ed. Engl. 34 (1995) 1348.
80. A.S. Guram, R.A. Rennels, S.L. Buchwald, Angew. Chem. 107 (1995) 1456; Angew. Chem. Int. Ed. Engl. 34 (1995) 1348.
81. Urgaonkar S., Xu J.-H., Verkade J.G. J. Org. Chem. 68:2003;8416
82. L.R. Titcomb, S. Caddick, F.G.N. Cloke, D.J. Wilson, D. McKerrecher, Chem. Commun. (2001) 1388.