1,1′-P/O-ferrocenyl ligands in palladium-catalyzed Suzuki coupling of aryl chlorides

Organometallics

Volumn 25, Issue 5, 2006, Pages 1199-1205

  Teo, Shihui ^a   Weng, Zhiqiang ^b   Hor, T S Andy ^b  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE MINERALS; CRYSTALLOGRAPHY; PALLADIUM; REACTION KINETICS;

ARYL CHLORIDES; PALLADIUM-CATALYZED SUZUKI COUPLING; SUZUKI CROSS-COUPLINGS;

MOLECULAR STRUCTURE;

EID: 33644899667     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050791j     Document Type: Article

References (57)

1. (a) Togni, A.; Hayashi, T. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; VCH: Weinheim, Germany, 1995; Chapter 1.
2. (b) Togni, A.; Haltermann, R. L. Metallocenes; Wiley-VCH: Weinheim, Germany, 1998.
3. (c) Long, N. J. Metallocenes: An Introduction to Sandwich Complexes; Blackwell Science: Oxford, U.K., 1998.
4. (a) Atkinson, R. C. J.; Gibson, V. C.; Long, N. J. Chem. Soc. Rev, 2004, 33, 313.
5. (b) Gan, K. S.; Hör, T. S. A. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; VCH: Weinheim, Germany, 1995.
6. (c) Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
7. (d) Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659.
8. (a) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359.
9. (b) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
10. (c) Hiyashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
11. Ohmura, H.; Matsuhashi, H.; Tanaka, M.; Kuroboshi, M.; Hiyama, T.; Hatanka, Y.; Goda, K.-I. J. Organomet. Chem. 1995, 499, 167.
12. (a) Josen, J. F.; Johannson, M. Org. Lett. 2003, 5(17), 3025.
13. (b) Pederson, H. L.; Johannsen, M. Chem. Commun. 1999, 2517.
14. (c) Pederson, H. L.; Johannsen, M. J. Org. Chem. 2002, 67, 7892.
15. Atkinson, R. C. J.; Gibson, V. C.; Long, N. J.; White, A. J. P.; Williams, D. J. Organometallics 2004, 23, 2744.
16. (a) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem, 1999, 64, 6797.
17. (b) Bei, X.; Uno, T.; Morris, J. H.; Turner, W.; Weinberg, W. H.; Guram, A. S. Organometallics 1999, 18, 1840.
18. (c) Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 1922.
19. (d) Dai, W. M.; Li, Y.; Zhang, Y.; Lai, K. W.; Wu, J. Tetrahedron Lett. 2004, 45, 1999.
20. (e) Dai, W. M.; Yeung, K. K. Y.; Wang, Y. Tetrahedron 2004, 60, 4425.
21. (f) Hayashi, T. Acta Chem. Scad. 1996, 50, 259.
22. (g) Hayashi, T. Acc. Chem. Res, 2000, 33, 354.
23. (h) Dai, W.-M.; Zhang, Y. Tetrahedron Lett. 2005, 46, 1377.
24. Braunstein, P.; Naud, F. Angew. Chem., Int. Ed. 2001, 40, 680.
25. Weng, Z.; Teo, S.; Koh, L. L.; Hor, T. S. A. Organometallics 2004, 23, 4342.
26. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
27. (b) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2001.
28. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
29. (d) Miyamura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
30. (a) Moulton, R. D.; Bard, A. J. Organometallics 1988, 7, 351.
31. (b) Dong, T.-Y.; Lai, L.-L. J. Organomet. Chem. 1996, 509, 131.
32. (c) Dong, T.-Y.; Lai, L.-L. Synthesis 1995, 1231.
33. For ferrocene-based monophosphine ligands in Suzuki cross-coupling of aryl chlorides, see: (a) Pickett, T. E.; Richards, J. C. Tetrahedron Lett. 2001, 42, 3767.
34. (b) Liu, S. Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408.
35. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
36. (d) Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592.
37. See for example: (a) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
38. (b) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
39. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
40. (d) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746.
41. (a) Galardon, E.; Ramdeedul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760.
42. (b) Nishihara, Y.; Onodera, H.; Osakada, K. Chem. Commun. 2004, 192.
43. (a) Cammidge, A. N.; Crépy, K. V. L. Tetrahedron 2004, 60, 4377.
44. (b) Cammidge, A. N.; Crépy, K. V. L. J. Org. Chem. 2003, 67, 6832.
45. (c) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
46. (a) B - Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944.
47. (b) Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184.
48. (c) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2398.
49. (a) Kastrup, C. J.; Oldfield, S. V.; Rzepa, H. S. Dalton Trans. 2002, 2421.
50. (b) Moore, J. W.; Pearson, R. G. Kinetics and Mechanism; Wiley: New York, 1981; p 304.
51. (a) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
52. (b) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
53. Echavarren, A. M.; Cárdenas, D. J. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; VCH: Weinheim, Germany, 2004; Chapter 1.
54. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
55. SMART, version 5.1; Bruker Analytical X-ray Systems, Madison, WI, 2000.
56. Sheldrick, G. M. SADABS, a Program for Empirical Absorption Correction; University of Göttingen, Göttingen, Germany, 2000.
57. SHELXTL, version 5.03; Bruker Analytical X-ray Systems, Madison, WI, 1997.