Cationic, neutral, and anionic platinum(II) complexes based on an electron-rich PNN ligand. New modes of reactivity based on pincer hemilability and dearomatization

Organometallics

Volumn 27, Issue 11, 2008, Pages 2627-2634

  Vuzman, Dana ^a   Poverenov, Elena ^a   Shimon, Linda J W ^a   Diskin Posner, Yael ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; PLATINUM; PLATINUM COMPOUNDS;

DEAROMATIZATION; ELECTRON-RICH; HEMILABILITY; NEW MODES; PLATINUM(II) COMPLEXES; REACTIVITY (CHEMICAL); SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

DYES;

EID: 45449102310     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8001069     Document Type: Article

References (83)

1. For recent reviews on pincer-type complexes, see:(a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
2. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
3. (c) Jensen, C. M. Chem. Commun. 1999, 2443.
4. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837.
5. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798.
6. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870.
7. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 445.
8. (h) Rybtchinski, B.; Milstein, D. ACS Symp. Ser. 2004, 885, 70.
9. (a) Kawatsura, M.; Hartwig, J. F. Organometallics 2001, 20, 1960.
10. (b) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677.
11. (c) Gibson, D. H.; Pariya, C.; Mashuta, M. S. Organometallics 2004, 23, 2510.
12. (d) Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Organometallics 2006, 25, 3007.
13. (e) Benito-Garagori, D.; Becker, E.; Wiederman, J.; Lackner, W.; Pollak, M.; Mereiter, K.; Kisala, J.; Kirchner, K. Organometallics 2006, 25, 1900.
14. (f) Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Angew. Chem., Int. Ed. 2007, 46, 4736.
15. (g) Benito-Garagorri, D.; Wiederman, J.; Pollak, M.; Mereiter, K.; Kirchner, K. Organometallics 2007, 26, 217.
16. iPrPNP: (a) Jansen, A.; Pitter, S. Monatsch. Chem. 1999, 130, 783.
17. (b) Trovitch, R. J.; Lobkovsky, E.; Chirik, P. J. Inorg. Chem. 2006, 45, 7252.
18. (c) Ref 5e.
19. (a) Hermann, D.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. Organometallics 2002, 21, 812.
20. (b) Ben-Ari, E.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 4714.
21. (c) Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Milstein, D. Organometallics 2004, 23, 4026.
22. (d) Ben-Ari, E.; Cohen, R.; Gandelman, M.; Shimon, L. J. W.; Martin, J. M. L.; Milstein, D. Organometallics 2006, 25, 3190.
23. (f) Feller, M.; Karton, A.; Leitus, G.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390.
24. (g) Ben-Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390.
25. (h) Feller, M.; Ben-Ari, E.; Gupta, T,; Shimon, L. J. W.; Leitus, G.; Diskin-Posner, Y.; Weiner, L.; Milstein, D. Inorg. Chem. 2007, 46, 10479.
26. (a) Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 12429.
27. (b) Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113.
28. (e) Zhang, J.; Gandelman, M.; Herrman, D.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Inorg. Chim. Acta 2006, 359, 1955.
29. Examples of hemilabile pincer complexes: (a) Choualeb, A.; Lough, A. J.; Gusev, D. G. Organometallics 2007, 26, 5224.
30. (b) Gomez-Benitez, V.; Toscano, R. A.; Morales-Morales, D. Inorg. Chem. Commun. 2007, 10, 1.
31. (c) Poverenov, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2005, 24, 5937.
32. (d) Rybtchinski, B.; Oevers, S.; Montag, M.; Vigalok, A.; Rozenberg, H.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 9064.
33. (e) Van Koten, G. Pure Appl. Chem. 1989, 61, 1681.
34. Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. 1994, 33, 497.
35. (a) Gandelman, M.; Rybtchinski, B.; Ashkenazi, N.; Gauvin, R.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 5372.
36. (b) Cohen, R.; Rybtchinski, B.; Gandelman, M.; Martin, J. M. L; Milstein, D. J. Am. Chem. Soc. 2003, 125, 6532.
37. (c) Gandelman, M.; Vigalok, A.; Shimon, L. J. W.; Milstein, D. Organometallics 1997, 16, 3981.
38. (d) Gandelman, M.; Shimon, L. J. W.; Milstein, D. Chem. Eur. J. 2003, 9, 4295.
39. (e) Gandelman, M.; Milstein, D. Chem. Commun. 2000, 1603.
40. (f) Gandelman, M.; Vigalok, A.; Kontantinovski, L.; Milstein, D. J. Am. Chem. Soc. 2000, 122, 9848.
41. (a) Poverenov, E.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Ben-David, Y.; Milstein, D. Chem. Eur. J. 2004, 10, 4673.
42. (b) Poverenov, E.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Ben-David, Y.; Milstein, D. Organometallics 2005, 24, 1082.
43. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790.
44. The outer-sphere chloride is disordered and appears in a few different positions.
45. Crabtree, R. H. The Organometalic Chemistry of the Transition Metals; Wiley: New York, 2005.
46. Sacco, A.; Vasapollo, G.; Nobile, C. F.; Piergiovanni, A.; Pellinghelli, M. A.; Lanfranchi, A. J. Organomet. Chem. 1988, 356, 397.
47. (a) Gorla, F.; Venanzi, L. M.; Albinati, A. Organometallics 1994, 13, 43.
48. (b) Hahn, C.; Spiegier, M.; Herdtweck, E.; Taube, R. Eur. J. Inorg. Chem. 1998, 1425.
49. (a) King, R. B. Adv. Organometal. Chem. 1964, 2, 157.
50. (b) Theopold, K. H.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 2489.
51. (c) Theopold, K. H.; Bergman, R. G. Organometallics 1982, 1, 219.
52. (d) Krause, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 2972.
53. (a) Anders, U.; Graham, W. A. G. Chem. Commun. 1966, 291.
54. (b) Tachikawa, M.; Sievert, A. C.; Muetterties, E. L.; Thompson, M. R.; Day, C. S.; Day, V. W. J. Am. Chem. Soc. 1980, 102, 1725.
55. (c) Tachikawa, M.; Geerts, R. L.; Muetterties, E. L. J. Organomet. Chem. 1981, 213, 11.
56. (a) Kraus, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 2972.
57. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Application of Organotransition Metal Chemistry; Univerity Science Books: Mill Valley, CA, 1987.
58. (a) Rice, G. W.; Tobias, R. S. J. Am. Chem. Soc. 1977, 99, 2141.
59. (b) Nakazawa, H.; Ozawa, F.; Yamamoto, A. Organometallics 1983, 2, 241.
60. (c) Garcia, M. P.; Oro, L. A.; Lahoz, F. J. Angew. Chem. 1988, 100, 1766.
61. Angew. Chem., Int. Ed. Engl. 1988, 27, 1700.
62. (d) Brunet, J. J.; Commenges, G.; Neibecker, D.; Rosenberg, L. J. Organomet. Chem. 1996, 522, 117.
63. (e) Gusev, D. G.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 1998, 120, 13138.
64. Dedieu, A. Transition Metal Hydrides; VCH: Weinheim, 1991; p 361.
65. (a) Benfield, F. W. S.; Fonder, R. A.; Green, M. L. H.; Moser, G. A.; Prout, K. J. Chem. Soc., Chem. Commun. 1973, 759.
66. (b) Francis, B. R.; Green, M. L. H.; Tuyet, L.; Moser, G. A. J. Chem. Soc., Dalton Trans. 1976, 1339.
67. (a) Pez, G. P.; Grey, R. A.; Corsi, J. J. Am. Chem. Soc. 1981, 103, 7528.
68. (b) Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1981, 103, 7536.
69. (c) Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1980, 102, 5949.
70. Gaus, P. L.; Kao, S. C.; Youngdahl, K.; Darensbourg, M. Y. J. Am. Chem. Soc. 1985, 107, 2428.
71. (a) Bruno, J. W.; Huffman, J. C.; Green, M. A.; Caulton, K. G. J. Am. Chem. Soc. 1984, 106, 8310.
72. (b) Del Paggio, A. A.; Andersen, R. A.; Muetterties, E. L. Organometallics 1987, 6, 1260.
73. (a) Fernández, S.; Fornie's, J.; Gil, B.; Gomez, J.; Lalinde, E. Dalton Trans. 2003, 822.
74. (b) Berenguer, J. R.; Lalinde, E.; Torroba, J. Inorg. Chem. 2007, 46, 9919.
75. (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
76. (b) Ingleson, M. J.; Pink, M.; Caulton, K. G. J. Am. Chem. Soc. 2006, 128, 4248.
77. Formation of methane was detected by GC/MS. Its origin is not clear.
78. nBuLi with complex 2 substitution of the chloride to form the hydride complex 3 took place (rather than formation of an anionic product) might be a result of the β-elimination process. Thus, an anionic butyl complex, analogous to 5, might be formed first, followed by a β-H elimination process that involves chloride loss.
79. 25b
80. (a) Ellis, J. E.; Faltynek, R. A. J. Am. Chem. Soc. 1977, 99, 1801.
81. (b) Reinartz, S.; Brookhart, M.; Templeton, J. L. Organometallics 2002, 21, 247.
82. While complexes 7 and 8 are highly stable at room temperature, they completely decompose during 72 h at 60°C (complex 7) and 72 h at 90°C (complex 8).
83. Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411.