Synthesis and characterization of organopalladium complexes containing a fluoro ligand

Organometallics

Volumn 17, Issue 9, 1998, Pages 1774-1781

  Pilon, Mark C ^a   Grushin, Vladimir V ^a,b  

^a WILFRID LAURIER UNIVERSITY   (Canada)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003277763     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9708440     Document Type: Article

References (78)

1. (a) Doherty, N. M.; Hoffman, N. W. Chem. Rev. 1991, 91, 553.
2. (b) Witt, M.; Roesky, H. W. Prog. Inorg. Chem. 1992, 40, 353.
3. Holloway, J. H.; Hope, E. G. J. Fluorine Chem. 1996, 76, 209.
4. Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373.
5. (a) Hudlicky, M. J. Fluorine Chem. 1989, 44, 345.
6. (b) For homogeneous, catalytic C-F bond activation, see: Aizenberg, M.; Milstein, D. Science 1994, 265, 359; J. Am. Chem. Soc. 1995, 777, 8674.
7. (b) For homogeneous, catalytic C-F bond activation, see: Aizenberg, M.; Milstein, D. Science 1994, 265, 359; J. Am. Chem. Soc. 1995, 777, 8674.
8. For a recent monograph, see: Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995.
9. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis. The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes; Wiley: New York, 1992.
10. (b) Wiessermel, K.; Arpe, H.-J. Industrial Organic Chemistry; VCH: New York, 1993.
11. 7f
12. (b) Leary, K.; Templeton, D. H.; Zalkin, A.; Bartlett, N. Inorg Chem. 1973, 12, 1726.
13. (c) Alter, E. Z. Anorg. Allg. Chem. 1974, 408, 115.
14. (d) Wright, A. F.; Fender, B. E. F.; Bartlett, N.; Leary, K. Inorg. Chem. 1978, 17, 748.
15. (e) Tressaud, A.; Soubeyroux, J. L.; Touhara, H.; Demazeau, G.; Langlais, F. Mater. Res. Bull. 1981, 16, 207.
16. (f) Bachmann, B.; Mueller, B. G. Z. Anorg. Allg. Chem. 1991, 597, 9.
17. Peacock, R. D.; Kemmitt, R. D. W.; Stocks, J. J. Chem. Soc. A 1971, 846.
18. Doyle, G. J. Organomet. Chem. 1982, 224, 355.
19. (a) Dixon, K. R.; McFarland, J. J. J. Chem. Soc., Chem. Commun. 1972, 1274.
20. (b) Cairns, M. A.; Dixon, K. R.; McFarland, J. J. J. Chem. Soc., Dalton Trans. 1975, 1159.
21. Mason, M. R.; Verkade, J. G. Organometallics 1990, 9, 864; 1992, 11, 2212.
22. Mason, M. R.; Verkade, J. G. Organometallics 1990, 9, 864; 1992, 11, 2212.
23. Fraser, S. L.; Antipin, M. Yu.; Khroustalyov, V. N.; Grushin, V. V. J. Am. Chem. Soc. 1997, 119, 4769.
24. (a) McClinton, M. A. Aldrichim. Acta 1995, 28, 31 and references cited therein.
25. 2Ru(H)(FHF)] as the major product, see: Whittlesey, M. K; Perutz, R. N.; Greener, B.; Moore, M. H. J. Chem. Soc., Chem. Commun. 1997, 187.
26. (a) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890.
27. (b) Grushin, V. V.; Bensimon, C.; Alper, H. Organometallics 1995,14, 3259.
28. (a) Coulson, D. R. J. Am. Chem. Soc. 1976, 98, 3111.
29. (b) Hintermann, S.; Pregosin, P. S.; Rüegger, H.; Clark, H. C. J. Organomet. Chem. 1992, 435, 225.
30. (c) Roesky, H. W.; Sotoodeh, M.; Xu, Y. M.; Schrumpf, F.; Noltemeyer, M. Z. Anorg. Allg. Chem. 1990, 580, 131.
31. (d) Murphy, V. J.; Hascall, T.; Chen, J. Y.; Parkin, G. J. Am. Chem. Soc. 1996, 118, 7428.
32. (a) Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6131.
33. (b) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441 and references cited therein.
34. Bryndza, H. E.; Tarn, W. Chem. Rev. 1988, 88, 1163.
35. Gilje, J. W.; Roesky, H. W. Chem. Rev. 1994, 94, 895.
36. Bergman, R. G. Polyhedron 1995, 14, 3227.
37. (a) Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
38. (b) Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115.
39. CRC Handbook of Chemistry and Physics, 57th ed.; Weast, R. C., Ed.; CRC Press: Cleveland, 1976; p D-75.
40. (a) Grushin, V. V. Angew.Chem. 1998, in press.
41. (b) Flemming, J. P.; Pilon, M. C.; Borbulevitch, O. Ya.; Antipin, M. Yu.; Grushin, V. V. Inorg Chim. Acta 1998, in press.
42. Araghizadeh, F.; Branan, D. M.; Hoffman, N. W.; Jones, J. H.; McElroy, E. A.; Miller, N. C.; Ramage, D. L.; Salazar, A. B.; Young, S. H. Inorg. Chem. 1988, 27, 3752. Branan, D. M.; Hoffman N. W.; McElroy, E. A; Miller, N. C.; Ramage, D. L.; Schott, A. F.; Young, S. H. Inorg Chem. 1987, 26, 2915.
43. Araghizadeh, F.; Branan, D. M.; Hoffman, N. W.; Jones, J. H.; McElroy, E. A.; Miller, N. C.; Ramage, D. L.; Salazar, A. B.; Young, S. H. Inorg. Chem. 1988, 27, 3752. Branan, D. M.; Hoffman N. W.; McElroy, E. A; Miller, N. C.; Ramage, D. L.; Schott, A. F.; Young, S. H. Inorg Chem. 1987, 26, 2915.
44. 31P NMR spectra of the reaction mixtures exhibited slightly broadened singlet resonances for the fluoro complexes (see text).
45. (b) Silver(I) fluoride originating from aqueous solutions always contains some amounts of water which is virtually impossible to remove, see: Horn, E.; Snow, M. R. Aust. J. Chem. 1980, 33, 2369.
46. Kurran, W.; Musco, A. lnorg. Chim. Acta 1975, 12, 187. Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
47. Kurran, W.; Musco, A. lnorg. Chim. Acta 1975, 12, 187. Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
48. Lancashire, R. J. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1987; Vol. 5, p 775.
49. Klopman, G. In Chemical Reactivity and Reaction Paths; Klopman, G., Ed.; John Wiley and Sons: New York, 1974; p 55.
50. 5 under nitrogen for at least 24 h prior to use.
51. 29b
52. (b) Harris, R. K. Nuclear Magnetic Resonance Spectroscopy: A Physicochemical View; Longman Scientific & Technical: Harlow, 1986.
53. Portnoy, M.; Ben-David, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465.
54. 2 by rotary evaporation (15-30 min at ambient temperature) and keeping the resulting solution at ca. -15 to -20 °C overnight.
55. Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605.
56. 3N.
57. 2] (R = Ph or Me) is shifted almost entirely toward the dimer, the palladium fluoride remains the only thermodynamically favored species when dissolved in dichloromethane saturated with water (Scheme 2).
58. (b) Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242.
59. 40b
60. (b) Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Organic Solvents. Physical Properties and Methods of Purification, 4th ed.; Wiley: New York, 1986; p 490-491.
61. The lack of correlation cannot be accounted for by impurities in the fluoro complexes used for the VT NMR studies. Two recrystallizations of 7 from dichloromethane-hexane did not affect the temperature of coalescence. No difference in the VT NMR behavior was observed for similarly prepared wet dichloromethane solutions of 1 originating from the TREAT HF and AgF reactions.
62. 31P NMR.
63. For examples of hydrogen bonds to fluoro ligands in transition metal complexes, see: Richmond, T. G. Coord. Chem. Rev. 1990, 105, 221.
64. (a) Veltheer, J. E.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 12478.
65. 2O.
66. P-F= 8.3 Hz).
67. 41b effects may be responsible for an increase in the positive charge on the metal center.
68. (b) Manna, J.; Kuehl, C. J.; Whiteford, J. A; Stang, P. J. Organometallics 1997, 16, 1897.
69. Caulton, K. G. New J. Chem. 1994, 18, 25.
70. 2O to the metal center. As a result, the water-induced ligand exchange in 7 is noticeably slower than in 1.
71. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley: NewYork, 1992. Bunton, C. A. Nucleophilic Substitution at a Saturated Carbon Atom; Elsevier: New York, 1963.
72. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley: NewYork, 1992. Bunton, C. A. Nucleophilic Substitution at a Saturated Carbon Atom; Elsevier: New York, 1963.
73. Reutov, O. A.; Beletskaya, I. P. Reaction Mechanisms of Organometallic Compounds; North-Holland: Amsterdam, 1968. Makarova, L. G.; Nesmeyanov, A. N. The Organic Compounds of Mercury; North-Holland: Amsterdam, 1967.
74. Reutov, O. A.; Beletskaya, I. P. Reaction Mechanisms of Organometallic Compounds; North-Holland: Amsterdam, 1968. Makarova, L. G.; Nesmeyanov, A. N. The Organic Compounds of Mercury; North-Holland: Amsterdam, 1967.
75. Ioele, M.; Ortaggi, G.; Scarsella, M.; Sleiter, G. Polyhedron 1991, 10, 2475.
76. --free, the benzene solution of the Pd(0) complex can be washed with a few portions of water. However, because the washing must be done under nitrogen, we found this less convenient than simply adding solid NaI to the mixture.
77. 4Cl)] should be thoroughly extracted with dichloromethane and/or hot benzene.
78. 1H NMR spectral patterns.