Mechanism of C-P reductive elimination from trans-[Pd(CH=CHPh)Br(PMePh2)2]

Organometallics

Volumn 28, Issue 8, 2009, Pages 2527-2534

  Wakioka, Masayuki ^a   Nakajima, Yumiko ^a   Ozawa, Fumiyuki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; ISOMERS; PALLADIUM; SOLVENTS; SULFUR COMPOUNDS;

DFT CALCULATION; HIGH SELECTIVITY; KINETICS AND THERMODYNAMICS; NON-POLAR; OXIDATIVE ADDITIONS; POLAR SOLVENTS; PRE-DISSOCIATION; REDUCTIVE ELIMINATION; SOLVENT POLARITY;

X RAY DIFFRACTION ANALYSIS;

EID: 84962394018     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om801207k     Document Type: Article

References (75)

1. (a) Ozawa, F. In Current Methods in Inorganic Chemistry Volume3, Fundamentals of Molecular Catalysis; Yamamoto, A., Kurosawa, H., Eds.; Elsevier Science: Amsterdam, The Netherlands, 2003; Chapter 9.
2. (b) Crabtree, R. H. The Organometallic Chemistry ofthe Transition Metals, 4th ed.; John Wiley & Sons: Hoboken, NJ, 2005; pp 55-60.
3. (c) Yamamoto, A. Organotransition Metal Chemistry, Fundamental Concepts and Application; John Wiley & Sons: New York, NY, 1986; pp 240-245.
4. (d) 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; pp 323-353.
5. (e) Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031-1046.
6. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
7. (b) Hartwig, J. F. Inorg. Chem. 2007, 46, 1936-1947.
8. (c) Hartwig, J. F. Nature 2008, 455, 314-322.
9. (a) Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313-6315.
10. (b) (Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441-12453.
11. (c) Grushin, V. V. Organometallics 2000, 19, 1888-1900.
12. (d) Herrmann, W. A.; Brossmer, C.; Priermeier, T.; Oefele, K. J. Organomet. Chem. 1994, 481, 97-108.
13. (e) Segelstein, B. E.; Bulter, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12-13.
14. (f) Sakamoto, M.; Shimizu, I.; Yamamoto, A. Chem. Lett. 1995, 1101-1102.
15. (g) Vicente, J.; Abad, J.- A.; Martinez-Viviente, E.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 2000, 19, 752-760.
16. (h) Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 555-562.
17. (i) Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 6166-6169.
18. (j) Macgregor, S. A. Chem. Soc. Rev. 2007, 36, 67-76.
19. (a) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
20. (b) Migita, T.; Nagai, T.; Kiuchi, K.; Kosugi, M. Bull. Chem. Soc. Jpn. 1983, 56, 2869-2870.
21. (c) Clark, J. H.; Tavener, S. J.; Barlow, S. J. J. Mater. Chem. 1995, 5, 827-830.
22. (d) Vicente, J.; Abad, J.-A.; Frankland, A. D.; De Arellano, M. C. R. Chem.-Eur. J. 1999, 5, 3066-3075.
23. (e) Bourgogne, C.; Le, F. Y.; Juen, P.; Masson, P.; Nicoud, J.-F.; Masse, R. Chem. Mater. 2000, 12, 1025-1033.
24. (f) Lambert, C.; Gaschler, W.; Noll, G.; Weber, M.; Schmalzlin, E.; Brauchle, C.; Meerholz, K. J. Chem. Soc., Perkin Trans. 2 2001, 6, 964-974.
25. (g) de la Torre, G.; Gouloumis, A.; Vazquez, P.; Torres, T. Angew. Chem., Int. Ed. 2001, 40, 2895-2898.
26. (h) Cheng, Z.; Subbarayan, M.; Chen, X.; Gambhir, S. S. J. Label. Compd. Radiopharm. 2005, 48, 131-137.
27. (i) Marcoux, D.; Charette, A. B. J. Org. Chem. 2008, 73, 590-593.
28. (a) Huang, C.-C.; Duan, J.-P.; Wu, M.-Y.; Liao, F.-L.; Wang, S.-L.; Cheng, C.-H. Organometallics 1998, 17, 676-682.
29. (b) Rybin, L. V.; Petrovskaya, E. A.; Rubinskaya, M. I.; Kuz'mina, L. G.; Struchkov, Y. T.; Kaverin, V. V.; Koneva, N. Y. J. Organomet. Chem. 1985, 288, 119-129.
30. (c) Kowalski, M. H.; Hinkle, R. J.; Stang, P. J. J. Org. Chem. 1989, 54, 2783-2784.
31. (d) Hinkle, R. J.; Stang, P. J.; Kowalski, M. H. J. Org. Chem. 1990, 55, 5033-5036.
32. (e) Dervisi, A.; Edwards, P. G.; Newman, P. D.; Tooze, R. P. Dalton 2000, 523-528.
33. (f) Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387-2388.
34. (g) Jutand, A.; Negri, S. Organometallics 2003, 22, 4229-4237.
35. (a) Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2006, 128, 50-51.
36. (b) Arisawa, M.; Yamaguchi, M. Adv. Synth. Catal. 2001, 343, 27-28.
37. (a) Kwong, F. Y.; Chan, K. S. Organometallics 2000, 19, 2058-2060.
38. (b) Kwong, F. Y.; Chan, K. S. Chem. Commun. 2000, 1069-1070.
39. (c) Kwong, F. Y.; Lai, C. W.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 10285-10289.
40. (d) Kwong, F. Y.; Chan, K. S. Organometallics 2001, 20, 2570-2578.
41. (e) Lai, C. W.; Kwong, F. Y.; Wang, Y.; Chan, K. S. Tetrahedron Lett. 2001, 42, 4883-4885.
42. (f) Kwong, F. Y.; Lai, C. W.; Chan, K. S. Tetrahedron Lett. 2002, 43, 3537-3539.
43. (g) Kwong, F. Y.; Lai, C. W.; Yu, M.; Tian, Y.; Chan, K. S. Tetrahedron 2003, 59, 10295-10305.
44. (h) Kwong, F. Y.; Lai, C. W.; Yu, M.; Chan, K. S. Tetrahedron 2004, 60, 5635-5645.
45. (i) Wang, Y.; Lai, C. W.; Kwong, F. Y.; Jia, W.; Chan, K. S. Tetrahedron 2004, 60, 9433-9439.
46. An alternative mechanism involving a phosphido intermediate has been proposed for the conversion of trans-[PdMe(I)(PPh3)2] to [PdPh(I)- (PMePh2)(PPh3)]: Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576-8581.
47. The mechanism of C-P reductive elimination of anionic phosphorus ligands such as phosphido and phosphonato has been examined using isolated complexes: (a) Gaumont, A.-C.; Brown, J. M.; Hursthouse, M. B.; Coles, S. J. Chem. Commun. 1999, 63-64.
48. (b) Adam, M.; Stockland, R. A., Jr.; Clark, R.; Guzei, I. Organometallics 2002, 21, 3278-3284.
49. (c) Stockland, R. A., Jr.; Levine, A. M.; Giovine, M. T.; Guzei, I. A.; Cannistra, J. C. Organometallics 2004, 23, 647-656.
50. (d) Kohler, M. C.; Stockland, R. A., Jr.; Rath, N. P. Organometallics 2006, 25, 5746-5756.
51. (e) Kalek, M.; Stawinski, J. Organometallics 2008, 27, 5876-5888.
52. The C-P reductive elimination of a styryl complex has been reported for trans-[Pd{CH=CHPh-(/E)|Br(PPh3)2](1b).5a
53. Wakioka, M.; Nagao, M.; Ozawa, F. Organometallics 2008, 27, 602-608.
54. The PPh3 analogue [Pd]n2-(E)-PhCH=CHPPh3|(PPh3)2]Br ((E)- 3b) has been reported.5a
55. A metallophosphorane intermediate has been proposed for F/Ph exchange of [RhF(PPh3)3] affording [RhPh(PFPh2)(PPh3)2]. Macgregor, S. A.; Roe, D. C.; Marshall, W. J.; Bloch, K. M.; Bakhmutov, V. I.; Grushin, V. V. J. Am. Chem. Soc. 2005, 127, 15304-15321.
56. (a) Loar, M. K.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4174-4181.
57. (b) Brown, J. M.; Cooley, N. A. Organoemtallics 1990, 9, 353-359.
58. (c) Calhorda, M. J.; Brown, J. M.; Cooley, N. A. Organometallics 1991, 10, 1431-1438.
59. (d) Ozawa, F.; Tani, T.; Katayama, H. Organometallics 2005, 24, 2511-2515.
60. Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 220-223.
61. Dolby, L. J.; Wilkins, C.; Frey, T. G. J. Org. Chem. 1966, 31, 1110-1116.
62. Taillefer, M.; Cristau, H. J.; Fruchier, A.; Vicente, V. J. Organomet. Chem. 2001, 624, 307-315.
63. Ukai, T.; Kawamura, H.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253-266.
64. Beurskens, P. T.; Beurskens, G.; de Gelder, R.; Garcla-Grana, S.; Gould, R. O.; Israel, R.; Smits, J. M. M. The DIRDIF99 Program System; University of Nijmegen: The Netherlands, 1999.
65. Sheldrick, G. M. SHELXL-97; University of Gottingen: Germany, 1997.
66. (a) Becke, A. D. Phys. Rev.A 1988, 38, 3098-3100.
67. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785-789.
68. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
69. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
70. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
71. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2004.
72. (a) Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117-119.
73. (b) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
74. (c) Tomasi, J.; Cammi, R. J. Comput. Chem. 1995, 16, 1449-1458.
75. Glendening, E. D.; Read, A. E.; Carpenter, J. E.; Weinhold, F. NBO(version 3.1); Gaussian, Inc.: Pittsburgh, PA, 2004.