Study of insertion of olefins and/or carbon monoxide into phosphine-imine palladium methyl complexes

Organometallics

Volumn 20, Issue 7, 2001, Pages 1292-1299

  Reddy, K Rajender ^a   Surekha, K ^a   Lee, Gene Hsiang ^a   Peng, Shie Ming ^a   Chen, Jwu Ting ^a   Liu, Shiuh Tzung ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE-IMINE PALLADIUM METHYL COMPLEXES; X-RAY STRUCTURES;

CARBON MONOXIDE; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; PALLADIUM COMPOUNDS; POLYMERIZATION;

ORGANOMETALLICS;

EID: 0035795460     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000880q     Document Type: Article

References (76)

1. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
2. (b) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, Germany, 1996; Vol. 1.
3. (a) Ittel, S.D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169.
4. (b) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. Angew. Chem., Int. Ed. 2000, 38, 428.
5. (c) Drent, E.; Budzelaar, P.H.M. Chem. Rev. 1996, 663.
6. (d) Cavell, K. J. Coord. Chem. Rev. 1996, 155, 209.
7. (e) Sen, A. Acc. Chem. Res. 1993, 26, 303.
8. For Pd-polyketone catalysts with symmetrical P-P ligands see: (a) Schwarz, J.; Herdtweck, E.; Herrmann, H.; Gardiner, M. G. Organometallics 2000, 19, 3154.
9. (b) Verspui, G.; Schanssema, F.; Sheldon, R. A. Angew. Chem., Int. Ed. 2000, 39, 804.
10. (c) Bianchini, C.; Lee, H. M.; Meli, A.; Oberhauser, W.; Vizza, F.; Bruggeller, P.; Haid, R.; Langes, C. Chem. Commun. 2000, 777.
11. (d) Doherty, S.; Eastham, G. R.; Tooze, R. P.; Scanlan, T. H.; Williams, D.; Elsegood, M. R. J.; Clegg, W. Organometallics 1999, 18, 3558.
12. (e) Safir, A. L.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 643.
13. (f) Kacker, S.; Jiang, Z.; Sen, A. Macromolecules 1996, 29, 5852.
14. (g) Abu-Surrah, A. S.; Wursche, R.; Rieger, B.; Eckert, G.; Pechhold, W. Macromolecules 1996, 4806.
15. (h) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455.
16. (i) Drent, E.; Van Breokhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
17. For Pd-polyketone catalysts with symmetrical N-N ligands see: (a) Milani, B.; Alessio, G.; Zangrando, E.; Randaccio, L.; Consiglio, G. J. Chem. Soc., Dalton Trans. 1996, 1021.
18. (b) Jiang, Z.; Adams, S. E.; Sen, A. Macromolecules 1994, 27, 2694.
19. (c) Sen, A.; Jiang, Z. Macromolecules 1993, 26, 911.
20. (d) Brookhart, M.; Rix, F. C.; DeSimone, J. M.; Barborak, J. C. J. Am. Chem. Soc. 1992, 114, 5894.
21. For CO and/or olefin insertion and mechanistic studies of Pd-complexes with P-P ligands see: (a) Shultz, C. S.; Ledford, J.; DeSimone, J. M.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6351.
22. (b) Barlow, G. K.; Boyle, J. D.; Cooley, N. A.; Ghaffar, T.; Wass, D. F. Organometallics 2000, 19, 1470.
23. (c) Parlevliet, F. J.; Zuideveld, M. A.; Kiener, G.; Kooijman, H.; Spek, A. L.; Kamer, P. C.; van Leeuwen, P. W. N. M. Organometallics 1999, 18, 3394.
24. (d) Zuideveled, M. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Klusener, P. A. A.; Stil, H. A.; Roobeek, C. F. J. Am. Chem. Soc. 1998, 120, 7977.
25. (e) Kacker, S.; Sen, A. J. Am. Chem. Soc. 1997, 119, 10028.
26. (f) Toth, I.; Elsevier, C. J. J. Am. Chem. Soc. 1993, 115, 10388.
27. (g) Batistini, A.; Consiglio, G. Organometallics 1992, 11, 1766.
28. (h) Dekker, G. P. C. M.; Elsevier; C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598.
29. (i) Dekker, G. P. C. M.; Elsevier: C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357.
30. (j) Ozawa, F.; Hayashi, T.; Koide, H.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1991, 1469.
31. For CO and/or olefin insertion and mechanistic studies of Pd-complexes with N-N ligands see: (a) Carfagna, C.; Formica, M.; Gatti, G.; Musco, A.; Pierleoni, A. J. Chem. Soc., Chem. Commun. 1998, 1113.
32. (b) Groen, J. H.; Delis, J. G. P.; van Leeuwen, P. W. N. M.; Vrieze, K. Organometallics 1997, 16, 68.
33. (c) Delis, J. G. P.; van Leeuwen, P. W. N. M.; Vrieze K.; Veldman, N.; Spek, A. L.; Fraanje, J.; Goubitz, K. J. Organomet. Chem. 1996, 514, 125.
34. (d) Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 4746.
35. (e) Markies, B. A.; Kruis, D.; Rietveld, M. H. P.; Verkerk, K. A. N.; Boersma, J.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; Van Koten, G. J. Am. Chem. Soc. 1995, 117, 5263.
36. (f) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137.
37. (g) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
38. (h) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Elsevier, C. J. J. Chem. Soc., Chem. Commun. 1993, 1203.
39. For theoretical studies on CO and olefin copolymers see: (a) Svensson, M.; Matsubara, T.; Morokuma, K. Organometallics 1996, 15, 5568.
40. (b) Margl, P.; Ziegler, T. Organometallics 1996, 15, 5519.
41. For CO and/or olefin insertion and catalytic studies with unsymetrical (P-P*)Pd-complexes see: (a) Gambs, C.; Chaloupka, S.; Consiglio, G.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 2486.
42. (b) Nozaki, K.; Hiyama, T.; Kacker, S.; Horvath, I. Organometallics 2000, 19, 2031.
43. (c) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12799.
44. (d) Keim, W.; Mass, H. J. Organomet. Chem. 1996, 514, 271.
45. (e) van Leeuwen, P. W. N. M.; Roobeek, C. F.; van der Heijden, H. J. Am. Chem. Soc. 1994, 116, 12117.
46. For CO and/or olefin insertion and catalytic studies with unsymmetrical (N-N*)Pd-complexes see: (a) Meneghetti, S. P.; Lutz, P. J.; Kress, J. Organometallics 1999, 18, 2734.
47. (b) Groen, J. H.; Vlaar, M.; van Leeuwen, P. W. N. M.; Vrieze, K.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1998, 551, 67.
48. (c) Rülke, R. E.; Delis, J. G. P.; Groot, A. M.; Elsevier, C. J.; van Leeuwen, P.W.N.M.; Vrieze K.; Goubitz, K.; Schenk, H. J. Organomet. Chem. 1996, 508, 109.
49. (d) Delis, J. G. P.; Rep, M.; Rulke, R. E.; van Leeuwen, P. W. N. M.; Vrieze, K.; Fraanje, J.; Goubitz, K. Inorg. Chim. Acta 1996, 250, 87.
50. For CO and/or olefin insertion and catalytic studies with unsymmetrical (N-O)Pd-complexes see: (a) Green, M. J.; Britovsek, G. J. P.; Cavell, K. J.; Gerhards, F.; Yates, B. F.; Frankcombe, K.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1998, 1137.
51. (b) Gree, M. J.; Bristovsek. G. J. P.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1996, 1563.
52. (c) Frankcombe, K.; Cavell, K.; Yates, B. J. Chem. Soc., Chem. Commun. 1996, 781.
53. (d) Hoare, J. L.; Cavell, K. J.; Hecker, R.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1996, 2197.
54. For CO and/or olefin insertion and catalytic studies with unsymmetrical (P-O)Pd-complexes see: (a) Braunstein, P.; Frison, C.; Morise, X. Angew. Chem., Int. Ed. 2000, 39, 2867, and references therein.
55. (b) Bristovsek, G. J. P.; Keim, W.; Mecking, S.; Sainz, D.; Wagner, T. J. Chem. Soc., Chem. Commun. 1993, 1632.
56. For catalytic studies with (P-)Pd-complexes see: (a) Braunstein, P.; Fryzuk, M. D.; Le Dall, M.; Naud, F.; Rettig, S. J.; Speiser, F. J. Chem Soc., Dalton Trans. 2000, 1067.
57. (b) van den Beuken, E. K.; Smeets, W. J. J.; Spek, A. L.; Feringa, B. L. Chem. Commun. 1998, 223.
58. (c) Aeby, A.; Gsponer, A.; Consiglio, G. J. Am. Chem. Soc. 1998, 120, 11000.
59. (d) Aeby, A.; Bangerter, F.; Consiglio, G. Helv. Chim. Acta 1998, 81, 764.
60. (e) Aeby, A.; Consiglio, G. Helv. Chim. Acta 1998, 81, 35.
61. (f) Sperrle, M.; Consiglio, G. Helv. Chim. Acta 1996, 79, 1387.
62. For insertion studies with (P-N)Pd-complexes see: (a) Brinkmann, P. H. P.; Luinstra, G. A. J. Organomet. Chem. 1999, 572, 193
63. (b) Aeby, A.; Consiglio, G. J. Chem. Soc., Dalton Trans. 1999, 655.
64. (c) Luinstra, G. A.; Brinkmann, P. H. P. Organometallics 1998, 17, 5160.
65. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C.H. Organometallics 1992, 11, 1937.
66. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336, and references therein.
67. Reddy, K. R.; Chen, C.-L.; Liu, Y.-H.; Peng, S.-M.; Chen, J.-T.; Liu, S.-T. Organometallics 1999, 18, 2574.
68. Cooper, M. K.; Downes, J. M.; Duckworth, P. A. Inorg. Synth. 1989, 25, 129.
69. Rulke, R. E.; Ernstring, J. M.; Spek, A. L.; Elsevier; C. J.; van Leeuwen, P. W. N. M., Vrieze, K. Inorg. Chem. 1993, 32, 5769.
70. Pelagatti, P.; Bacchi, A.; Carcelli, M.; Costa, M.; Fochi, A.; Ghidini, P.; Leporati, E.; Masi, M.; Pelizzi, C.; Pelizzi, G. J. Organomet. Chem. 1999, 583, 94.
71. Bhattacharyya, P.; Parr, J.; Slawin, A. M. Z. J. Chem. Soc., Dalton Trans. 1998, 3609.
72. Ankersmit, H. A.; Løken, B. H.; Kooijman, H.; Spek, A. L.; Vrieze, K.; van Koten, G. Inorg. Chim. Acta 1996, 252, 141.
73. Crociani, L.; Bandoli, G.; Dolmella, A.; Basato, M.; Corain, B. Eur. J. Inorg. Chem. 1998, 1811.
74. Braumbaugh, J. S.; Whittle, R. R.; Parvez, M.; Sen, A. Organometallics 1990, 98, 1735.
75. Pearson, R. G. Inorg. Chem. 1973, 12, 712.
76. Chen, J.-T.; Liu, S.-T.; Zhao, K.-Q. J. Chin. Chem. Soc. 2000, 47, 279.