Highly air-stable anionic mononuclear and neutral binuclear palladium(II) complexes for C-C and C-N bond-forming reactions

Inorganic Chemistry

Volumn 46, Issue 26, 2007, Pages 11316-11327

  Punji, Benudhar ^a   Mague, Joel T ^b   Balakrishna, Maravanji S ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38149138207     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701674x     Document Type: Article

References (67)

1. For examples, see: (a) Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum Press: New York, 1983.
2. (b) Applied Homogeneous Catalysis with Organornetallic Compounds; Cornils, B., Herrmann, W. H., Eds.; VCH: Weinheim, 1996.
3. (c) Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27-110.
4. (d) Balakrishna, M. S.; Reddy, V. S.; Krishnamurthy, S. S.; Nixon, J. F.; St. Laurent, J. C. T. R. B. Coord. Chem. Rev. 1994, 129, 1-90.
5. (e) Dilworth, J. R.; Wheatley, N. Coord. Chem. Rev. 2000, 199, 89-158.
6. (f) Appleby, T.; Woollins, J. D. Coord. Chem. Rev. 2002, 235, 121-140.
7. (g) Le Floch, P. Coord. Chem. Rev. 2006, 250, 627-681.
8. (h) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
9. (i) Suzuki, A. In Metal Catalysed Cross Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 49-97 and references therein.
10. (j) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
11. (a) Chatt, J.; Heaton, B. T. J. Chem. Soc. A 1968, 2745-2757. See also:
12. (b) Dixon, K. R.; Rattray, A. D. Can. J. Chem. 1971, 49, 3997-4004.
13. (c) Lindner, E.; Schilling, B. Chem. Ber. 1977, 110, 3266-3271.
14. Beaulieu, W. B.; Rauchfuss, T. B.; Roundhill, D. M. Inorg. Chem. 1975, 14, 1732-1734.
15. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516.
16. (b) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650.
17. (c) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681.
18. (d) Arif, A. M.; Bright, T. A.; Jones, R. A. J. Coord. Chem. 1987, 16, 45-50.
19. (e) Cobley, C. J.; van den Heuvel, M.; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467-2470.
20. (f) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657-8660.
21. (g) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Z. Z. Naturforsch. B 1994, 49, 801-811.
22. (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
23. (b) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
24. (c) Grushin, V. V.; Alper, H. Topics in Organometallic Chemistry; Murai, S., Ed.; Springer: New York, 1999: Vol. 3, pp 193-226 and references there in.
25. Mercado, R. M. L.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Organometallics 1999, 18, 906-914.
26. Punji, B.; Mague, J. T.; Balakrishna, M. S. Inorg. Chem. 2006, 45, 9454-9464.
27. Davies, A. R.; Dronsfield, A. T.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc., Perkin Trans. 1973, 1, 379-385.
28. Drew, D.; Doyle, J. R. Inorg. Synth. 1990, 28, 346-349.
29. Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411-428.
30. SMART, Version 5.625; Bruker-AXS: Madison, WI, 2000.
31. SAINT+, Version 6.35A; Bruker-AXS: Madison, WI, 2002.
32. Sheldrick, G. M. SADABS, Version 2.05; University of Göttingen: Göttingen, Germany, 2002.
33. (a) SHELXTL, Version 6.10; Bruker-AXS: Madison, WI, 2000.
34. (b) Sheldrick, G. M. SHELXS97 and SHELXL97; University of Göttingen: Göttingen, Germany, 1997.
35. Balakrishna, M. S.; Panda, R.; Mague, J. T. Inorg. Chem. 2001, 40, 5620-5625.
36. (a) Balakrishna, M. S.; Krishnamurthy, S. S. Ind. J. Chem. 1991, 30A, 536-537.
37. (b) Burrows, A. D.; Mahon, M. F.; Palmer, M. T.; Varrone, M. Inorg. Chem. 2002, 41, 1695-1697.
38. (c) Priya, S.; Balakrishna, M. S.; Mague, J. T. J. Organomet. Chem. 2003, 679, 116-124.
39. (a) Dubrovina, N. V.; Borner, A. Angew. Chem., Int. Ed. 2004, 43, 5883-5886.
40. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc 2000, 122, 5407-5408.
41. (c) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572.
42. (d) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196-4198.
43. (e) Ackermann, L.; Born, R.; Spatz, J. H.; Meyer, D. Angew. Chem., Int. Ed. 2005, 44, 7216-7219.
44. (f) Levine, A. M.; Stockland, R. A.; Clark, R.; Guzei, I. Organometallics 2002, 21, 3278-3284.
45. (g) Stockland, R. A.; Levine, A. M.; Giovine, M. T.; Guzei, I. A.; Cannistra, J. C. Organometallics 2004, 23, 647-656.
46. (h) Pryjomska, I.; Bartosz-Bechowski, H.; Ciunik, Z.; Trzeciak, A. M.; Ziòlkowski, J. J. Dalton Trans. 2006, 213-220.
47. (a) Slawin, A. M. Z.; Wainwright, M.; Woollins, J. D. J. Chem. Soc., Dalton Trans. 2002, 513-519.
48. (b) Calabrò, G.; Drommi, D.; Graiff, C.; Faraone, F.; Tiripicchio, A. Eur. J. Inorg. Chem. 2004, 1447-1453.
49. (c) Balakrishna, M. S.; George, P. P.; Mague, J. T. J. Organomet. Chem. 2004, 689, 3388-3394.
50. Calabrò, G.; Drommi, D.; Bruno, G.; Faraone, F. Dalton Trans. 2004, 81-89.
51. (a) Sherlock, D. J.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1997, 36, 5082-5089.
52. (b) Sherlock, D. J.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1997, 119, 1317-1322.
53. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
54. Sutton, L. Tables of Interatomic Distances and Configuration in Molecules and Ions; Special Publication Nos. 11 and 18; The Chemical Society: London, 1958 and 1965.
55. Day, R. O.; Prakasha, T. K.; Holmes, R. R.; Eckert, H. Organometallics 1994, 13, 1285-1293.
56. Chang, C.; Lin, Y.; Lee, G.; Wang, Y. J. Chem. Soc. Dalton Trans. 1999, 4223-4230.
57. Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885-3896.
58. Colacot, T. J.; Qian, H.; Cea-Olivares, R.; Hernandez-Ortega, S. J. Organomet. Chem. 2001, 637-639, 691-697.
59. Piechaczyk, O.; Doux, M.; Ricard, L.; Le Floch, P. Organometallics 2005, 24, 1204-1213.
60. (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2413-2416.
61. (b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
62. (c) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
63. (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
64. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
65. Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375-8384.
66. (a) Widegren, J. A.; Bennett, M. A.; Finke, R. G. J. Am. Chem. Soc. 2003, 125, 10301-10310.
67. (b) Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317-341.