Highly efficient cyclopalladated ferrocenylimine catalyst for Suzuki cross-coupling reaction of 3-pyridylboronic pinacol ester with aryl halides

Journal of Organometallic Chemistry

Volumn 691, Issue 6, 2006, Pages 1301-1306

  Zhang, Jinli ^a   Zhao, Liang ^a   Song, Maoping ^a   Mak, Thomas C W ^a   Wu, Yangjie ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

3 Pyridyl biaryl system; 3 Pyridylboronic pinacol ester; Cyclopalladated ferrocenylimine; Suzuki reaction

Indexed keywords

INERT GASES; ORGANIC COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

3-PYRIDYL BIARYL SYSTEM; CYCLOPALLADATED FERROCENYLIMINE; SUZUKI REACTION;

CATALYSTS;

EID: 32644447309     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.11.027     Document Type: Short Survey

References (62)

1. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
2. A. Suzuki F. Diederich P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim, Germany (Chapter 2)
3. S.P. Stanforth Tetrahedron 54 1998 263
4. A. Suzuki J. Organomet. Chem. 576 1999 147
5. A. Suzuki J. Organomet. Chem. 653 2002 83
6. Applications of phosphine ligands in homogeneous catalysis: G.W. Parshall, and S. Ittel Homogeneous Catalysis 1992 Wiley New York
7. L.H. Pignolet Homogeneous Catalysis with Metal Phosphine Complexes 1983 Plenum New York
8. M.R. Netherton, C. Dai, K. Neuschutz, and G.C. Fu J. Am. Chem. Soc. 123 2001 10099
9. J. Yin, M.P. Rainka, X.X. Zhang, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 1162
10. J.P. Stambuli, R. Kuwano, and J.F. Hartwig Angew. Chem., Int. Ed. 41 2002 4746
11. J.P. Wolfe, R.A. Singer, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9550
12. X. Bei, H.W. Turner, W.H. Weinberg, A.S. Guram, and J.L. Petersen J. Org. Chem. 64 1999 6797
13. A. Zapf, A. Ehrentraut, and M. Beller Angew. Chem., Int. Ed. 39 2000 4153
14. T.E. Pickett, and C.J. Richards Tetrahedron Lett. 42 2001 3767
15. M. Feuerstein, D. Laurenti, C. Bougeant, H. Doucet, and M. Santelli Chem. Commun. 2001 325
16. M. Feuerstein, H. Doucet, and M. Santelli Synlett 2001 1458
17. S.Y. Liu, M.J. Choi, and G.C. Fu Chem. Commun. 2001 2408
18. A. Zapf, and M. Beller Chem. Eur. J. 6 2000 1830
19. G.Y. Li Angew. Chem., Int. Ed. 40 2001 1513
20. B. Tao, and D.W. Boykin J. Org. Chem. 69 2004 4330
21. J.H. Li, and W.J. Liu Org. Lett. 6 2004 2809
22. T. Mino, Y. Shirae, M. Sakamoto, and T. Fujita J. Org. Chem. 70 2005 2191
23. J. Dupont, M. Pfeffer, and J. Spencer Eur. J. Inorg. Chem. 2001 1917
24. J. Dupont, C.S. Consorti, and J. Spencer Chem. Rev. 105 2005 2527
25. M. Beller, H. Fischer, W.A. Herrmann, K. Ofele, and C. Brossmer Angew. Chem., Int. Ed. Engl. 34 1995 1848
26. D.A. Albisson, R.B. Bedford, S.E. Lawrence, and P.N. Scully Chem. Commun. 1998 2095
27. R.B. Bedford, and S.L. Welch Chem. Commun. 2001 129
28. S. Gibson, D.F. Foster, G.R. Eastham, R.P. Tooze, and D.J. Cole-Hamilton Chem. Commun. 2001 779
29. W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Organomet. Chem. 576 1999 23
30. C. Zhang, J. Huang, M.L. Trudell, and S.P. Nolan J. Org. Chem. 64 1999 3804
31. C. Zhang, and M.L. Trudell Tetrahedron Lett. 41 2000 595
32. D.S. McGuinness, and K.J. Cavell Organometallics 19 2000 741
33. D. Zim, A.S. Gruber, G. Ebeling, J. Dupont, and A.L. Monteiro Org. Lett. 2 2000 2881
34. D.A. Alonso, C. Najera, and M.C. Pacheco J. Org. Chem. 67 2002 5588
35. H. Weissman, and D. Milstein Chem. Commun. 1999 1901
36. S.Q. Huo, Y.J. Wu, C.X. Du, Y. Zhu, H.Z. Yuan, and X.A. Mao J. Orangomet. Chem. 483 1994 139
37. X.L. Cui, Y.J. Wu, and L.R. Yang Chin. Chem. Lett. 10 1999 127
38. Y.J. Wu, J.J. Hou, H.Y. Yun, X.L. Cui, and R.J. Yuan J. Organomet. Chem. 637-639 2001 793
39. J.J. Hou, L.R. Yang, X.L. Cui, and Y.J. Wu Chin. J. Chem. 21 2003 717
40. L.R. Yang, J.L. Zhang, M.P. Song, S.S. Zhang, N. Yu, and Y.J. Wu Acta Chim. Sinica 61 2003 959
41. Y.J. Wu, L.R. Yang, J.L. Zhang, M. Wang, L. Zhao, M.P. Song, and J.F. Gong Arkivoc ix 2004 111
42. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633
43. D.S. Matteson J. Organomet. Chem. 581 1999 51
44. F. Kerins, and D.F. O'Shea J. Org. Chem. 67 2002 4968
45. C.L. Cioffi, W.T. Spencer, J.J. Richards, and R.J. Herr J. Org. Chem. 69 2004 2210
46. R.B. Bedford, and C.S.J. Cazin Chem. Commun. 2001 1540
47. R.B. Bedford, S.L. Hazelwood, and M.E. Limmert Chem. Commun. 2002 2610
48. A.F. Littke, and G.C. Fu J. Org. Chem. 64 1999 10
49. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 37 1998 3387
50. W.J. Li, D.P. Nelson, M.S. Jensen, R.S. Hoerrner, D.W. Cai, R.D. Larsen, and P.J. Reider J. Org. Chem. 67 2002 5394
51. N.M. Ali, A. McKillop, M.B. Mitchell, R.A. Rebelo, and P.J. Wallbank Tetrahedron 48 1992 8117
52. M. Ishikura, M. Kamada, and M. Terashima Heterocycles 229 1984 265
53. H. Shigyo, S. Sato, K. Shibuya, Y. Takahashi, T. Yamaguchi, H. Sonki, and T. Ohta Chem. Pharm. Bull. 41 1993 1573
54. M. Janka, G.K. Anderson, and N.P. Rath Inorg. Chim. Acta 357 2004 2339
55. U. Hacksell, L.E. Arvidsson, U. Svensson, J.L.G. Nilsson, D. Sanchez, H. Wikstrom, P. Lindberg, S. Hjorth, and A. Carlsson J. Med. Chem. 24 1981 1475
56. J. Srogl, G.D. Allred, and L.S. Liebeskind J. Am. Chem. Soc. 119 1997 12376
57. K. Inada, and N. Miyaura Tetrahedron 56 2000 8661
58. G. Semple, B.M. Andersson, V. Chhajlani, J. Georgsson, M. Johansson, M. Lindschoten, F. Pontén, Å. Rosenquist, H. Sörensen, L. Swanson, and M. Swanson Bioorg. Med. Chem. Lett. 12 2002 197
59. M.P. Trova, World Patent 0322219, 2003.
60. L.K. Klemn, and J. Dorsey J. Heterocycl. Chem. 28 1991 1153
61. B. Macchia, D.B. Bylund, V. Calderone, G. Giannaccini, A. Lucacchini, M. Macchia, A. Martinelli, E. Martinotti, E. Orlandini, F. Romagnoli, and A. Rossello Eur. J. Med. Chem. 33 1998 911
62. N. Shimizu, T. Kitamura, K. Watanabe, T. Yamaguchi, H. Shigyo, and T. Ohta Tetrahedron Lett. 34 1993 3421