Highly trifluoromethylated platinum compounds

Chemistry - A European Journal

Volumn 17, Issue 29, 2011, Pages 8085-8097

  Martínez Salvador, Sonia ^a   Forniés, Juan ^a   Martín, Antonio ^a   Menjón, Babil ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

fluorinated ligands; NMR spectroscopy; octahedral compounds; platinum; trifluoromethylation

Indexed keywords

ANIONIC LIGANDS; FLUORINATED LIGANDS; HOMOLEPTIC; OCTAHEDRAL COMPOUNDS; ORGANOELEMENT COMPOUNDS; ORGANOPLATINUM; OXIDATIVE ADDITIONS; TETRAHYDROTHIOPHENE; THERMALLY STABLE; TRIFLUOROMETHYL; TRIFLUOROMETHYLATION; WEAKLY COORDINATING ANIONS; X-RAY DIFFRACTION METHOD;

BROMINE; CHLORINE; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM; SALTS; TRANSITION METAL COMPOUNDS; X RAY DIFFRACTION;

PLATINUM COMPOUNDS;

EID: 79959947633     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100626     Document Type: Article

References (114)

1. R. P. Hughes, J. Fluorine Chem. 2010, 131, 1059
2. F. G. A. Stone, J. Fluorine Chem. 1999, 100, 227
3. R. P. Hughes, Adv. Organomet. Chem. 1990, 31, 183
4. J. C. Tatlow, J. Fluorine Chem. 1984, 25, 99
5. R. Nyholm, Q. Revs. Chem. Soc. 1970, 24, 1
6. F. G. A. Stone, Endeavour 1966, 25, 33
7. R. D. Chambers, T. Chivers, Organomet. Chem. Rev. 1966, 1, 279
8. P. M. Treichel, F. G. A. Stone, Adv. Organomet. Chem. 1964, 1, 143
9. R. E. Banks, R. N. Haszeldine, Adv. Inorg. Chem. Radiochem. 1961, 3, 337
10. J. J. Lagowski, Q. Revs. Chem. Soc. 1959, 13, 233.
11. E. R. Sigurdson, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1977, 812.
12. A. L. Galyer, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1976, 2235
13. L. Galyer, K. Mertis, G. Wilkinson, J. Organomet. Chem. 1975, 85, C 37.
14. V. Pfennig, N. Robertson, K. Seppelt, Angew. Chem. 1997, 109, 1410
15. Angew. Chem. Int. Ed. Engl. 1997, 36, 1350
16. J. F. Gibson, G. M. Lack, K. Mertis, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1976, 1492
17. K. Mertis, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1976, 1488.
18. R. D. Dresdner, T. J. Mao, J. A. Young, J. Am. Chem. Soc. 1958, 80, 3007
19. R. D. Dresdner, J. Am. Chem. Soc. 1956, 78, 876
20. R. Dresdner, J. Am. Chem. Soc. 1955, 77, 6633.
21. R. J. Lagow, J. A. Morrison, Adv. Inorg. Chem. Radiochem. 1980, 23, 177.
22. R. J. Lagow, J. L. Margrave, Prog. Inorg. Chem. 1979, 26, 161
23. E. K. Liu, R. J. Lagow, J. Chem. Soc. Chem. Commun. 1977, 450
24. N. J. Maraschin, B. D. Catsikis, L. H. Davis, G. Jarvinen, R. J. Lagow, J. Am. Chem. Soc. 1975, 97, 513
25. N. J. Maraschin, R. J. Lagow, Inorg. Chem. 1973, 12, 1458.
26. T. J. Juhlke, J. I. Glanz, R. J. Lagow, Inorg. Chem. 1989, 28, 980
27. R. A. Jacob, L. L. Gerchman, T. J. Juhlke, R. J. Lagow, J. Chem. Soc. Chem. Commun. 1979, 128
28. R. J. Lagow, L. L. Gerchman, R. A. Jacob, J. A. Morrison, J. Am. Chem. Soc. 1975, 97, 518.
29. D. Naumann, H. Butler, J. Fisher, J. Hanke, J. Mogias, B. Wilkes, Z. anorg. allg. Chem. 1992, 608, 69
30. L. J. Krause, J. A. Morrison, J. Am. Chem. Soc. 1981, 103, 2995
31. R. J. Lagow, R. Eujen, L. L. Gerchman, J. A. Morrison, J. Am. Chem. Soc. 1978, 100, 1722.
32. E. Bernhardt, G. Henkel, H. Willner, G. Pawelke, H. Bürger, Chem. Eur. J. 2001, 7, 4696.
33. D. Naumann, N. V. Kirij, N. Maggiarosa, W. Tyrra, Y. L. Yagupolskii, M. S. Wickleder, Z. anorg. allg. Chem. 2004, 630, 746.
34. B. Menjón, S. Martínez-Salvador, M. A. Gómez-Saso, J. Forniés, L. R. Falvello, A. Martín, A. Tsipis, Chem. Eur. J. 2009, 15, 6371.
35. N. Maggiarosa, W. Tyrra, D. Naumann, N. V. Kirij, Y. L. Yagupolskii, Angew. Chem. 1999, 111, 2392
36. Angew. Chem. Int. Ed. 1999, 38, 2252.
37. D. Naumann, W. Tyrra, J. Organomet. Chem. 1989, 368, 131.
38. D. Naumann, T. Roy, K.-F. Tebbe, W. Crump, Angew. Chem. 1993, 105, 1555
39. Angew. Chem. Int. Ed. Engl. 1993, 32, 1482.
40. W. Dukat, D. Naumann, Rev. Chim. Miner. 1986, 23, 589.
41. E. Bernhardt, M. Finze, H. Willner, J. Fluorine Chem. 2004, 125, 967
42. J. A. Schlueter, J. M. Williams, U. Geiser, J. D. Dudek, S. A. Sirchio, M. E. Kelly, J. S. Gregar, W. H. Kwok, J. A. Fendrich, J. E. Schirber, W. R. Bayless, D. Naumann, T. Roy, J. Chem. Soc. Chem. Commun. 1995, 1311.
43. U. Preiss, I. Krossing, Z. anorg. allg. Chem. 2007, 633, 1639
44. J. A. Schlueter, U. Geiser, A. M. Kini, H. H. Wang, J. M. Williams, D. Naumann, T. Roy, B. Hoge, R. Eujen, Coord. Chem. Rev. 1999, 190-192, 781.
45. S. Balters, E. Bernhardt, H. Willner, T. Berends, Z. Anorg. Allg. Chem. 2004, 630, 257
46. S. Balters, DPhil Thesis, University of Wuppertal (Germany), 2005 [urn:nbn:de:hbz:468-20050702].
47. R. J. Lagow, L. L. Gerchman, R. A. Jacob, (Massachusetts Institute of Technology, Cambridge, MA), US-A 3992424, 1976, p. 7; [
48. R. J. Lagow, L. L. Gerchman, R. A. Jacob, Chem. Abstr. 1977, 86, 72887 ]
49. R. J. Lagow, L. L. Gerchman, R. A. Jacob, (Massachusetts Institute of Technology, Cambridge, MA), US-A 3954585, 1976, p. 8; [
50. R. J. Lagow, L. L. Gerchman, R. A. Jacob, Chem. Abstr. 1976, 85, 160324 ].
51. J. A. Morrison, Adv. Inorg. Chem. Radiochem. 1983, 27, 293.
52. R. P. Hughes, R. B. Laritchev, L. N. Zakharov, A. L. Rheingold, Organometallics 2005, 24, 4845
53. R. P. Hughes, S. M. Maddock, I. A. Guzei, L. M. Liable-Sands, A. L. Rheingold, J. Am. Chem. Soc. 2001, 123, 3279
54. R. P. Hughes, J. T. Sweetser, M. D. Tawa, A. Williamson, C. D. Incarvito, B. Rhatigan, A. L. Rheingold, G. Rossi, Organometallics 2001, 20, 3800
55. R. P. Hughes, T. le Husebo, A. L. Rheingold, L. M. Liable-Sands, G. P. A. Yap, Organometallics 1997, 16, 5; see also
56. J. Banus, H. J. Emeléus, R. N. Haszeldine, J. Chem. Soc. 1951, 60.
57. R. Minkwitz, R. Bröchler, M. Berkei, Z. anorg. allg. Chem. 1996, 622, 1749.
58. N. V. Kirij, Y. L. Yagupolskii, N. Maggiarosa, W. Tyrra, D. Naumann, J. Fluorine Chem. 2001, 112, 213.
59. - are formed:, C. P. Andrieux, L. Gelis, M. Medebielle, J. Pinson, J. M. Saveant, J. Am. Chem. Soc. 1990, 112, 3509.
60. R. A. Rossi, A. B. Pierini, A. B. Peñéñory, Chem. Rev. 2003, 103, 71.
61. W. B. Farnham, Chem. Rev. 1996, 96, 1633. For recent evidence of the intermediacy of fluorinated carbanions in the chemistry of transition-metal compounds, see
62. B. D. Panthi, S. L. Gipson, A. Franken, Organometallics 2010, 29, 5890
63. J. G. Cordaro, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 16912; see also Ref. [24b].
64. r (usually known as dielectric constants), for the referred solvents at 25°C are quoted from:, C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3 rd ed., Wiley-VCH, Weinheim, 2003, Table A- 1, pp. 472- 475.
65. J. D. Atwood, Inorganic and Organometallic Reaction Mechanisms, 2 nd ed., Wiley, New York, 1997, Chapter 3, pp. 71-94.
66. J. A. Davies, F. R. Hartley, Chem. Rev. 1981, 81, 79.
67. S. F. Rach, F. E. Kühn, Chem. Rev. 2009, 109, 2061
68. B. N. Storhoff, H. C. Lewis, Jr., Coord. Chem. Rev. 1977, 23, 1.
69. +.
70. T. Yagyu, Y. Suzaki, K. Osakada, Organometallics 2002, 21, 2088.
71. J. D. Scollard, M. Day, J. A. Labinger, J. E. Bercaw, Helv. Chim. Acta 2001, 84, 3247.
72. T. G. Appleton, H. C. Clark, L. E. Manzer, Coord. Chem. Rev. 1973, 10, 335.
73. L. Johansson, O. B. Ryan, C. Rømming, M. Tilset, Organometallics 1998, 17, 3957.
74. P. Schützenberger, C. R. Hebd. Sceances Acad. Sci. 1870, 70, 1134
75. P. Schützenberger, Bull. Soc. Chim. Fr. 1868, 10, 188
76. P. Schützenberger, Ann. Chim. Phys. 1868, 15, 100.
77. D. B. dell'Amico, F. Calderazzo, G. dell'Amico, Gazz. Chim. Ital. 1977, 107, 101.
78. B. von Ahsen, R. Wartchow, H. Willner, V. Jonas, F. Aubke, Inorg. Chem. 2000, 39, 4424.
79. C. Crocker, P. L. Goggin, R. J. Goodfellow, J. Chem. Soc. Chem. Commun. 1978, 1056.
80. D. B. dell'Amico, F. Calderazzo, F. Marchetti, S. Merlino, J. Chem. Soc. Dalton Trans. 1982, 2257.
81. J. Forniés, M. A. Gómez-Saso, A. Martín, F. Martínez, B. Menjón, J. Navarrete, Organometallics 1997, 16, 6024.
82. N. Mina-Camilde, C. E. Manzanares, J. F. Caballero, J. Chem. Educ. 1996, 73, 804.
83. S. Martínez-Salvador, B. Menjón, J. Forniés, A. Martín, I. Usón, Angew. Chem. 2010, 122, 4382
84. Angew. Chem. Int. Ed. 2010, 49, 4286.
85. J. E. Huheey, E. A. Keiter, R. L. Keiter, Inorganic Chemistry, 4 th ed., Harper Collins, New York, 1993, pp. 182-199; see also
86. S. G. Bratsch, J. Chem. Educ. 1985, 62, 101
87. A. L. Allred, J. Inorg. Nucl. Chem. 1961, 17, 215.
88. J. Goodman, V. V. Grushin, R. B. Larichev, S. A. Macgregor, W. J. Marshall, D. C. Roe, J. Am. Chem. Soc. 2010, 132, 12013.
89. T. G. Appleton, M. H. Chisholm, H. C. Clark, L. E. Manzer, Inorg. Chem. 1972, 11, 1786.
90. D. S. Yang, G. M. Bancroft, R. J. Puddephatt, J. S. Tse, Inorg. Chem. 1990, 29, 2496.
91. Data (713) were retrieved from the Cambridge Structural Database (see Ref. [53]) that correspond to terminal Pt-CO derivatives regardless of the metal oxidation state, having rejected those structures with Pt-CO≤ as a valid criterion for linearity. Upper value of Pt-CO distance (199.4(3) pm):, E. E. Korshin, G. Leitus, L. J. W. Shimon, L. Konstantinovski, D. Milstein, Inorg. Chem. 2008, 47, 7177. Lower value of Pt-CO distance (162(4) pm)
92. A. Albinati, P. Leoni, L. Marchetti, S. Rizzato, Angew. Chem. 2003, 115, 6172
93. Angew. Chem. Int. Ed. 2003, 42, 5990. Upper value of ≡O distance (128.5 pm)
94. J. C. Calabrese, L. F. Dahl, P. Chini, G. Longoni, S. Martinengo, J. Am. Chem. Soc. 1974, 96, 2614. Lower value of ≡O distance (102(1) pm)
95. Z. Béni, R. Ros, A. Tassan, R. Scopelliti, R. Roulet, Dalton Trans. 2005, 315.
96. I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr. Sect. B 2002, 58, 389.
97. H. Willner, M. Bodenbinder, R. Bröchler, G. Hwang, S. J. Rettig, J. Trotter, B. von Ahsen, U. Westphal, V. Jonas, W. Thiel, F. Aubke, J. Am. Chem. Soc. 2001, 123, 588.
98. H. Willner, F. Aubke, Chem. Eur. J. 2003, 9, 1668
99. H. Willner, F. Aubke, Organometallics 2003, 22, 3612
100. H. Willner, F. Aubke, in Inorganic Chemistry Highlights (Eds.:, G. Meyer, L. Wesemann, D. Naumann,), Wiley-VCH, Weinheim, 2002, Chapter 11, pp. 195-212
101. H. Willner, F. Aubke, Angew. Chem. 1997, 109, 2506
102. Angew. Chem. Int. Ed. Engl. 1997, 36, 2402.
103. A. Bondi, J. Phys. Chem. 1964, 68, 441.
104. V. Y. Kukushkin, V. K. Bel'skii, E. A. Aleksandrova, E. Y. Pan'kova, V. E. Konovalov, V. N. Yakovlev, A. I. Moiseev, Zh. Obshch. Khim. 1991, 61, 318
105. V. Y. Kukushkin, V. K. Bel'skii, E. A. Aleksandrova, E. Y. Pan'kova, V. E. Konovalov, V. N. Yakovlev, A. I. Moiseev, Russ. J. Gen. Chem. 1991, 61, 284.
106. E. Pitcher, A. D. Buckingham, F. G. A. Stone, J. Chem. Phys. 1962, 36, 124.
107. W. E. Tyrra, J. Fluorine Chem. 2001, 112, 149.
108. J. Browning, P. L. Goggin, R. J. Goodfellow, M. G. Norton, A. J. M. Rattray, B. F. Taylor, J. Mink, J. Chem. Soc. Dalton Trans. 1977, 2061.
109. B. P. Andreini, D. B. dell'Amico, F. Calderazzo, M. G. Venturi, G. Pelizzi, A. Serge, J. Organomet. Chem. 1988, 354, 357.
110. D. R. Russell, P. A. Tucker, S. Wilson, J. Organomet. Chem. 1976, 104, 387.
111. M. Berkei, J. F. Bickley, B. T. Heaton, Z. Naturforsch. Teil B 2002, 57, 610.
112. W. C. Wolsey, J. Chem. Educ. 1973, 50, A 335.
113. CrysAlis RED: Program for X-ray CCD Camera Data Reduction, Version 1.171.32.19, Oxford Diffraction Ltd., Oxford, 2008.
114. G. M. Sheldrick, SHELXL-97: Program for the Refinement of Crystal Structures from Diffraction Data, University of Göttingen, Göttingen, 1997.