Generation and insertion reactivity of cationic palladium complexes that contain halogenated alkyl ligands

Organometallics

Volumn 23, Issue 3, 2004, Pages 600-609

  Foley, Stephen R ^a   Shen, Han ^a   Qadeer, Umair A ^a   Jordan, Richard F ^a  

^a THE UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; CHELATION; CHLORINE COMPOUNDS; COORDINATION REACTIONS; ETHYLENE; HALOGENATION; POLYMERIZATION; STEREOCHEMISTRY;

CATIONIC PALLADIUM COMPLEXES; HALOGENATED ALKYL LIGANDS; INSERTION POLYMERIZATION; INSERTION REACTIVITY;

PALLADIUM COMPOUNDS;

EID: 1142279574     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034211z     Document Type: Article

References (82)

1. (a) Stockland, R. A., Jr.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 6315.
2. (b) Foley, S. R.; Stockland, R. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350.
3. (c) Stockland, R. A., Jr.; Foley, S. R.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 796.
4. (d) Boffa, L. S.; Novak, B. M. Chem. Rev. 2000, 100, 1479.
5. (a) Strazisar, S. A.; Wolczanski, P. T. J. Am. Chem. Soc. 2001, 123, 4728.
6. (b) Watson, L. A.; Yandulov, D. V.; Caulton, K. G. J. Am. Chem. Soc. 2001, 123, 603.
7. (c) Boone, H.; Athey, P. S.; Mullins, M. J.; Philipp, D.; Muller, R.; Goddard, W. A. J. Am. Chem. Soc. 2002, 124, 8790.
8. (d) Kang, M.; Sen, A.; Zakharov, L.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12080.
9. Shen, H.; Jordan, R. F. Organometallics 2003, 22, 1878.
10. (a) Friedrich, H.; Moss, J. R. Adv. Organomet. Chem. 1991, 33, 235.
11. (b) Morrison, J. A. Adv. Organomet. Chem. 1993, 35, 211.
12. (a) McCrindle, R.; Arsenault, G. J.; Farwaha, R.; McAlees, A. J.; Sneddon, D. W. J. Chem. Soc., Dalton Trans. 1989, 761.
13. (b) McCrindle, R. Arsenault, G. J.; Farwaha, R.; Hampden-Smith, M. J.; Rice, R. E.; McAlees, A. J. Chem. Soc., Dalton Trans. 1988, 1773.
14. (c) McCrindle, R.; Arsenault, G. J.; Gupta, A.; Hampden-Smith, M. J.; Rice, R. E.; McAlees, A. J. J. Chem. Soc., Dalton Trans. 1991, 949.
15. (d) Ferguson, G.; Li, Y.; McAlees, A. J.; McCrindle, R.; Xiang, K. Organometallics 1999, 18, 2428.
16. (e) Ferguson, G.; Gallagher, J. F.; McAlees, A. J.; McCrindle, R. Organometallics 1997, 16, 1053.
17. (a) Hubbard, J. L.; Morneau, A.; Burns, R. M.; Nadeau, O. W. J. Am. Chem. Soc. 1991, 113, 9180.
18. (b) Ogino, H.; Shoji, M.; Abe, Y.; Shimura, M.; Shioni, M. Inorg. Chem. 1987, 26, 2542.
19. (c) Friedrich, H. B.; Moss, J. R. J. Organomet. Chem. 1993, 453, 85.
20. (d) Moss, J. R.; Niven, M. L.; Stretch, P. M. Inorg. Chim. Acta 1986, 119, 177.
21. (e) Haarman, H. F.; Ernsting, J. M.; Kranenburg, M.; Kooijman, H.; Veldman, N.; Spek, A. L.; van Leeuwen, P. W. N. M.; Vrieze, K. Organometallics 1997, 16, 887.
22. (f) Bergamini, P.; Bortolini, O.; Costa, E.; Pringle, O. G. Inorg. Chim. Acta 1996, 252, 33.
23. (g) Bradd, K. J.; Heaton, B. T.; Jacob, C.; Sampanthar, J. T.; Steiner, A. J. Chem. Soc., Dalton Trans. 1999, 1109.
24. (h) Leoni, P. Organometallics 1993, 12, 2431.
25. (i) Leoni, P.; Marchitti, F.; Paoletti, M. Organometallics 1997, 16, 2146.
26. (j) Mashima, K.; Fukumoto, A.; Nakano, H.; Kaneda, Y.; Tani, K.; Nakamura, A. J. Am. Chem. Soc. 1998, 120, 12151.
27. (k) Döhring, A.; Goddard, R.; Hopp, G.; Jolly, P. W.; Kokel, N.; Krüger, C. Inorg. Chim. Acta 1994, 222, 179.
28. (a) McCrindle, R.; Ferguson, G.; McAlees, A. J.; Arsenault, G. J.; Gupta, A.; Jennings, M. C. Organometallics 1995, 14, 2741.
29. (b) Hubbard, J. L.; McVicar, W. K. J. Organomet. Chem. 1992, 429, 369.
30. (c) Werner, H.; Wilfried, P.; Feser, R.; Zolk, R.; Thometzek, P. Chem. Ber. 1985, 118, 261.
31. (d) Hubbard, J. L.; McVicar, W. K. Organometallics 1990, 9, 2683.
32. (a) Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867.
33. (b) Belderrain, T.; Grubbs, R. H. Organometallics 1997, 16, 4001.
34. (c) Goldman, A. S.; Tyler, D. R. Organometallics 1984, 3, 449.
35. (d) Yang, M. X.; Sarkar, S.; Bent, B. E.; Bare, S. R.; Holbrook, M. T. Langmuir 1997, 13, 229.
36. (a) Axe, F. U.; Marynick, D. S. J. Am. Chem. Soc. 1988, 110, 3728.
37. (b) Cotton, J. D.; Markwell, R. D. J. Organomet. Chem. 1990, 388, 123.
38. (c) Cotton, J. D.; Crisp, G. T.; Daly, V. A. Inorg. Chim. Acta 1981, 47, 165.
39. (d) Cross, R. J.; Gemmill, J. J. Chem. Soc., Dalton Trans. 1981, 2317.
40. (e) Cawse, J. N.; Fiato, R. A.; Pruett, R. L. J. Organomet. Chem. 1979, 172, 405.
41. (f) Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67.
42. (g) Kuhlmann, E. J.; Alexander, J. J. Coord. Chem. Rev. 1980, 33, 195.
43. (h) Calderazzo, F.; Noack, K. Coord. Chem. Rev. 1966, 1, 118.
44. (i) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1986, 108, 6136.
45. Galamb, V.; Pályi, G.; Boese, R.; Schmid, G. Organometallics 1987, 6, 861.
46. (a) Burns, C. T.; Shen, H.; Jordan, R. F. J. Organomet. Chem. 2003, 638, 240.
47. (b) Burns, C. T.; Jordan, R. F. Abstr. Pap., Am. Chem. Soc. 2001, 222, 310-INOR.
48. Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663.
49. (a) Brookhart, M.; Rix, F. C.; DeSimone, J. M.; Barborak, J. C.; J. Am. Chem. Soc. 1992, 114, 5894.
50. (b) Tempel, D. J.; Johnson, L. K.; Huff, R. L.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6686.
51. 2 group of 4 apparently inhibits this process.
52. Lupinetti, A. J.; Strauss, S. H.; Frenking, G. Prog. Inorg. Chem. 2001, 49, 1.
53. Goldman, A. S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12159.
54. (a) Guo, Z.; Swenson, D. C.; Guram, A. S.; Jordan, R. F. Organometallics 1994, 13, 766.
55. (b) Shen, H.; Jordan, R. F. Organometallics 2003, 22, 2080.
56. (c) Guram, A. S.; Swenson, D. C.; Jordan, R. F. J. Am. Chem. Soc. 1992, 114, 8991.
57. Hughes, R. P.; Sweetser, J. T.; Tawa, M. D.; Williamson, A.; Incarvito, C. D.; Rhatigan, B.; Rheingold, A. L.; Rossi, G. Organometallics 2001, 20, 3800.
58. 3) even after 10 days at 75 °C, under which conditions 6 gradually decomposes.
59. Casey, C. P.; Carpenetti, D. W., II; Sakurai, H. Organometallics 2001, 20, 4262.
60. Shultz, C. S.; Ledford, J.; DeSimone, J. M.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6351.
61. +.
62. 2bipy or α-diimine) was observed. In some cases, the Cl content of the product exceeds the expected value, which is ascribed to reactions of the Pd byproducts with LiCl.
63. 2Cl was observed in the decomposition of 11.
64. Clemens, R. J. Chem. Rev. 1986, 86, 241.
65. (a) Weston, W. S.; Cole-Hamilton, D. J. Inorg. Chim. Acta 1998, 280, 99.
66. (b) Hommeltoft, S. I.; Baird, M. C. J. Am. Chem. Soc. 1985, 107, 2548.
67. Dilgassa, M.; Curtis, M. D. J. Organomet. Chem. 1979, 172, 177.
68. (a) Weston, W. S.; Lightfoot, P.; Cole-Hamilton, D. J. J. Organomet. Chem. 1998, 553, 473.
69. 2 and diketene, presumably by CO insertion and α-Cl elimination. Huser, M.; Francois, M.; Osborn, J. Fr. Patent 2637281, 1990.
70. For discussions of the factors that may influence insertion regioselectivity, see ref 3 and: (a) Michalak, A.; Ziegler, T. J. Am. Chem. Soc. 2001, 123, 12266.
71. (b) Michalak, A.; Ziegler, T. Organometallics 1999, 18, 3998.
72. (c) Michalak, A.; Ziegler, T. Organometallics 2000, 19, 1850.
73. (d) Deubel, D. V.; Ziegler, T. Organometallics 2002, 21, 4432.
74. (e) Deubel, D. V.; Ziegler, T. Organometallics 2002, 21, 1603.
75. (f) Philipp, D. M.; Muller, R. P.; Goddard, W. A., III; Storer, J.; McAdon, M.; Mullins, M. J. Am. Chem. Soc. 2002, 124, 10198.
76. (g) von Schenck, H.; Strömberg, S.; Zetterberg, K.; Ludwig, M.; Åkermark, B.; Svensson, M. Organometallics 2001, 20, 2813.
77. Tjaden, E. B.; Swenson, D. C.; Jordan, R. F. Organometallics 1995, 14, 371.
78. Belser, P.; Zelewsky, A. Helv. Chim. Acta 1980, 63, 1675.
79. Drew, D.; Doyle, J. R. Inorg. Synth. 1990, 28, 346.
80. (a) Black, T. H. Aldrichim. Acta 1983, 16, 3.
81. (b) Aldrich Technical Bulletin AL-180; Aldrich Chemical Co.: Milwaukee, WI, 2003, p 1 and references therein.
82. gNMR, version 4.1.2; Adept Scientific, Letchworth, U.K., 2000.