Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction

Journal of Organometallic Chemistry

Volumn 696, Issue 13, 2011, Pages 2669-2675

  Hajipour, Abdol R ^a,b   Rafiee, Fatemeh ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

Catalyst; Cyclopalladated complex; Heck reaction; Tribenzylamine

Indexed keywords

CATALYSTS; CHLORINE COMPOUNDS; ORGANOMETALLICS; PALLADIUM COMPOUNDS;

C-C CROSS-COUPLINGS; CROSS-COUPLED PRODUCT; CYCLOPALLADATED COMPLEXES; EFFICIENT CATALYSTS; HECK CROSS-COUPLING REACTION; HECK REACTIONS; SHORT REACTION TIME; TRIBENZYLAMINE;

CHEMICAL REACTIONS;

EID: 79957684265     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.03.023     Document Type: Short Survey

References (71)

1. R.F. Heck Palladium Reagents in Organic Synthesis 1985 Academic Press London
2. A. de Meijere, and F.E. Meyer Angew. Chem. 106 1994 2473
3. J. Tsuji Palladium Reagents and Catalysts 1995 Wiley Chichester
4. W.A. Herrmann B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds 1996 VCH Weinheim 712 726
5. S. Bräse, and A. de Meijere P.J. Stang, F. Diederich, Metal Catalyzed Cross Coupling Reactions 1997 Wiley-VCH Weinheim 99 166
6. R.R. Bader, P. Baumeister, and H.U. Blaser Chimia 50 1996 99
7. V.V. Grushin, and H. Alper Chem. Rev. 94 1994 1047
8. T.H. Riermeier, A. Zapf, and M. Beller Top. Catal. 4 1998 301
9. Y. Ben-David, M. Portnoy, M. Gozin, and D. Milstein Organometallics 11 1992 1995
10. M. Portnoy, Y. Ben-David, and D. Milstein Organometallics 12 1993 4734
11. J.B. Davison, N.M. Simon, and S.A. Sojka J. Mol. Catal. 22 1984 394
12. A. Spencer J. Organomet. Chem. 270 1984 115
13. M. Beller, and A. Zapf Synlett 1998 792
14. M. Julia, M. Duteil, C. Grard, and E. Kuntz Bull. Soc. Chim. Fr. 1973 2791
15. K. Kaneda, M. Higushi, and T. Imanaka J. Mol. Catal. 63 1990 33
16. M.T. Reetz, and G. Lohmer Chem. Commun. 1996 1921
17. M. Beller, H. Fischer, K. Kühlein, C.P. Reisinger, and W.A. Herrmann J. Organomet. Chem. 520 1996 257
18. M.T. Reetz, R. Breinbauer, and K. Wanninger Tetrahedron Lett. 37 1996 4499
19. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, and G.R.J. Artus Angew. Chem. 107 1995 2602
20. W.A. Herrmann, C.P. Reisinger, and M. Spiegler J. Organomet. Chem. 572 1998 93
21. G.D. Frey, J. Schutz, E. Herdtweck, and W.A. Herrmann Organometallics 24 2005 4416
22. W.A. Herrmann, C. Broßmer, K. Öfele, C.P. Reisinger, T. Priermeier, M. Beller, and H. Fischer Angew. Chem. 107 1995 1989
23. W.A. Herrmann, C. Broßmer, C.P. Reisinger, T.H. Riermeier, K. Öfele, and M. Beller Chem. - Eur. J. 3 1997 1357
24. W.A. Herrmann, V.P.W. Böhm, and C.P. Reisinger J. Organomet. Chem. 576 1999 23
25. G.D. Frey, C.P. Reisinger, E. Herdtweck, and W.A. Herrmann J. Organomet. Chem. 690 2005 3193 3201
26. M. Ohff, A. Ohff, M.E. van der Boom, and D. Milstein J. Am. Chem. Soc. 119 1997 11687
27. A. Gonzalez, C. Lopez, X. Solans, M. Font-Bardia, and E. Molins J. Organomet. Chem. 693 2008 2119
28. G.M. Lobmaier, G.D. Frey, R.D. Dewhurst, E. Herdtweck, and W.A. Herrmann Organometallics 26 2007 6290
29. A.J. Cheney, and B.L. Shaw J. Chem. Soc., Dalton Trans. 1972 754
30. B.L. Shaw New J. Chem. 22 1998 77
31. B.L. Shaw, S.D. Perera, and E.A. Staley Chem. Commun. 1998 136
32. G.J. Gainsford, and R. Mason J. Organomet. Chem. 80 1974 395
33. E.C. Alyea, S.A. Dias, G. Ferguson, and P.J. Roberts J. Chem. Soc., Dalton Trans. 1979 948
34. E.C. Alyea, G. Ferguson, J. Malito, and B.L. Ruhl Organometallics 8 1989 1188
35. T. Mitsudo, W. Fischetti, and R.F. Heck J. Org. Chem. 49 1984 640
36. A.D. Tanase, G.D. Frey, E. Herdtweck, S.D. Hoffmann, and W.A. Herrmann J. Organomet. Chem. 692 2007 3316
37. G. Aragay, J. Pons, J. García-Anton, X. Solans, M. Font-Bardia, and J. Ros J. Organomet. Chem. 693 2008 3396
38. A.D. Ryabov Synthesis 3 1985 233
39. M. Pfeffer Recl. Trav. Chim. Pays-Bas 109 1990 567
40. M. Pfeffer Pure Appl. Chem. 64 1992 335
41. J. Spencer, and M. Pfeffer Adv. Met. Org. Chem. 6 1998 103
42. V.V. Dunina, and O.N. Gorunova Russ. Chem. Rev. 73 2004 309
43. R.B. Bedford, and L.T. Pilarski Tetrahedron Lett. 49 2008 4216
44. R.B. Bedford, M. Betham, S.J. Coles, P.N. Horton, and M.J. Lopez-Saez Polyhedron 25 2006 1003
45. R.B. Bedford, M. Betham, M.E. Blake, R.M. Frost, P.N. Horton, M.B. Hursthousec, and R.M. López-Nicolás Dalton Trans. 16 2005 2774
46. D.A. Albisson, R.B. Bedford, S.E. Lawrence, and P.N. Scully Chem. Commun. 1998 2095
47. R.B. Bedford, M. Betham, J.P.H. Charmant, and A.L. Weeks Tetrahedron 64 2008 6038
48. R.B. Bedford, and M.E. Limmert J. Org. Chem. 68 2003 8669
49. J. Buey, and P. Espinet J. Organomet. Chem. 507 1996 137
50. K.K. Lo, C. Chung, T.K. Lee, L. Lui, K.H. Tang, and N. Zhu Inorg. Chem. 42 2003 6886
51. C. Lopez, A. Caubet, S. Perez, X. Solans, and M. Font-Bardía J. Organomet. Chem. 681 2003 80
52. S. Perez, C. Lopez, A. Caubet, X. Solans, M. Font-Bardía, A. Roig, and E. Molins Organometallics 25 2006 596
53. A. Moyano, M. Rosol, R.M. Moreno, C. Lopez, and M.A. Maestro Angew. Chem., Int. Ed. 44 2005 1865
54. F. Tjosaas, and A. Fiksdahl J. Organomet. Chem. 692 2007 5429
55. W.A. Herrmann, K. Öfele, D. von Preysing, and S.K. Schneider J. Organomet. Chem. 687 2003 229
56. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. Engl. 41 2002 4176
57. M. Huser, M.T. Youinou, and J.A. Osborn Angew. Chem., Int. Ed. Engl. 28 1989 1386
58. W.A. Herrmann, C. Broßmer, T. Priermeier, and K. Öfele J. Organomet. Chem. 481 1994 97
59. M. Keles, Z. Aydin, and O. Serindag J. Organomet. Chem. 692 2007 1951
60. H.V. Huynh, J.H.H. Ho, T.C. Neo, and L.L. Koh J. Organomet. Chem. 690 2005 3854
61. A.K. Gupta, C.H. Song, and C.H. Oh Tetrahedron Lett. 45 2004 4113
62. Y. Han, H.V. Huynh, and L.L. Koh J. Organomet. Chem. 692 2007 3606
63. Q. Xu, W.L. Duan, Z.Y. Lei, Z.B. Zhu, and M. Shi Tetrahedron 61 2005 11225
64. W. Chen, C. Xi, and Y. Wu J. Organomet. Chem. 692 2007 4381
65. A.R. Hajipour, K. Karami, and A. Pirisedigh J. Organomet. Chem. 694 2009 2548
66. A.R. Hajipour, K. Karami, and A. Pirisedigh Appl. Organomet. Chem. 23 2009 504
67. A.R. Hajipour, K. Karami, and Gh. Tavakoli Appl. Organomet. Chem. 24 2010 798
68. A.R. Hajipour, K. Karami, and A. Pirisedigh Appl. Organomet. Chem. 24 2010 454
69. A.R. Hajipour, K. Karami, and Gh. Tavakoli J. Organomet. Chem. 2010 (online)
70. Y. Fuchita, K. Yoshinaga, T. Hanaki, H. Kawano, and J. Kinoshita-Nagaoka J. Organomet. Chem. 580 1999 273
71. S.R. Dubbaka, and P. Vogel Chem. - Eur. J 11 2005 2633