Platinum(II) complexes with coordinated electron-withdrawing fluoroalkyl and fluoroaryl ligands: Synthesis, reactivity, and catalytic activity

Organometallics

Volumn 31, Issue 4, 2012, Pages 1257-1270

  Sgarbossa, Paolo ^a   Scarso, Alessandro ^b   Strukul, Giorgio ^b   Michelin, Rino A ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONWITHDRAWING; FLUOROARYL LIGANDS; LEWIS ACIDITY; METAL CENTERS; ORGANIC SUBSTRATE; PEROXOCOMPLEXES; PHOSPHINE COMPLEX; PLATINUM COMPLEXES;

CATALYST ACTIVITY; CATALYTIC OXIDATION; CHELATION; HYDROGEN PEROXIDE; LIGANDS; PHOSPHORUS COMPOUNDS; PLATINUM; TRANSITION METALS;

PLATINUM COMPOUNDS;

EID: 84857508580     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200953z     Document Type: Review

References (108)

1. Elschenbroich, C; Salzer, A. Organometallics: A Concise Introduction; VCH: Weinheim, Germany, 1989.
2. Ros, R.; Michelin, R. A.; Bataillard, R.; Roulet, R. J. Organomet. Chem. 1977, 139, 355-359
3. Ros, R.; Michelin, R. A.; Carturan, G.; Belluco, U. J. Organomet. Chem. 1977, 133, 213-218
4. Ros, R.; Michelin, R. A.; Bataillard, R.; Roulet, R. J. Organomet. Chem. 1978, 161, 75-90
5. Ros, R.; Michelin, R. A.; Bataillard, R.; Roulet, R. J. Organomet. Chem. 1979, 165, 107-116
6. Abis, L.; Sen, A.; Halpern, J. J. Am. Chem. Soc. 1978, 100, 2915-2916
7. Abis, L.; Santi, R.; Halpern, J. J. Organomet. Chem. 1981, 215, 263-267
8. Sostero, S.; Traverso, O.; Ros, R.; Michelin, R. A. J. Organomet. Chem. 1983, 246, 325-329
9. Green, M. L. H. Organometallic Compounds, 3 rd ed.; Methuen: London, 1968; Vol. 2, pp 263-271.
10. Hartley, F. R. The Chemistry of Platinum and Palladium; Applied Science: London, 1973; p 316.
11. Sheppard, W. A.; Sharts, C. M. Organic Fluorine Chemistry; W. A. Benjamin: New York, 1969.
12. Chambers, R. R. Fluorine in Organic Chemistry; Wiley: New York, 1973.
13. Rosevear, D. T.; Stone, F. G. A. J. Chem. Soc. A 1968, 164-167
14. Mukhedkar, A.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1969, 3023-3026
15. Hughes, R. P.; Overby, J. S.; Williamson, A.; Lam, K.-C.; Concolino, T. E.; Rheingold, A. L. Organometallics 2000, 19, 5190-5201
16. Michelin, R. A.; Napoli, M; Ros, R. J. Organomet. Chem. 1979, 175, 239-255
17. Bennett, M. A.; Chee, H.-K.; Robertson, G. B. Inorg. Chem. 1979, 18, 1061-1070
18. Michelin, R. A.; Ros, R. J. Chem. Soc., Dalton Trans. 1989, 1149-1159 and references therein
19. Sinigalia, R.; Michelin, R. A.; Pinna, F.; Strukul, G. Organometallics 1987, 6, 728-734
20. Strukul, G.; Sinigalia, R.; Zanardo, A; Pinna, F.; Michelin, R. A. Inorg. Chem. 1989, 28, 554-559
21. Zanardo, A; Michelin, R. A.; Pinna, F.; Strukul, G. Inorg. Chem. 1989, 28, 1648-1653
22. Clark, H. C.; Ruddick, J. D. Inorg. Chem. 1970, 9, 2556-2562
23. Uson, R.; Fornies, J.; Espinet, P.; Alfranca, G. Synth. React. Inorg. Met.-Org. Chem. 1980, 10, 579-590
24. Uson, R.; Fornies, J.; Martinez, F.; Tomas, M. J. Chem. Soc., Dalton Trans. 1980, 888-894
25. Hughes, R. P.; Ward, A. J.; Golen, J. A.; Incarnito, C. D.; Rheingold, A. L.; Zakharov, L. N. Dalton Trans. 2004, 2720-2727
26. Pizzo, E.; Sgarbossa, P.; Scarso, A.; Michelin, R. A.; Strukul, G. Organometallics 2006, 25, 3056-3062
27. Bennett, M. A.; Chee, H.-K.; Jefferey, J. C.; Robertson, G. B. Inorg. Chem. 1979, 18, 1071-1076
28. Hall, M. B.; Fenske, R. F. Inorg. Chem. 1972, 11, 768-779
29. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422
30. Otto, S. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2001, C57, 793-795
31. Khanna, A.; Khandelwal, B. L.; Saxena, A. K.; Singh, T. P. Polyhedron 1995, 14, 2705-2710
32. Al-Fawaz, A.; Aldridge, S.; Coombs, D. L.; Dickinson, A. A.; Willock, D. J.; Ooi, L.-l.; Light, M. E.; Coles, S. J.; Hursthouse, M. B. Dalton Trans. 2004, 4030-4037
33. Del Pra, A.; Zanotti, G.; Bombieri, G.; Ros, R. Inorg. Chim. Acta 1979, 36, 121-125
34. Johansson, M. H.; Otto, S. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, C56, e12-e15
35. Michelin, R. A.; Belluco, U.; Ros, R. Inorg. Chim. Acta 1977, 24, L33-L34
36. Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, C17-C20
37. Michelin, R. A.; Faglia, S.; Uguagliati, P. Inorg. Chem. 1983, 22, 1831-1834
38. Michelin, R. A.; Bertani, R.; Mozzon, M.; Zanotto, L.; Benetollo, F.; Bombieri, G. Organometallics 1990, 9, 1149-1459
39. Reger, D. L.; Dukes, M. D. J. Organomet. Chem. 1978, 153, 67-72
40. Clark, G. R.; Hoskins, S. V.; Roper, W. R. J. Organomet. Chem. 1982, 234, C9-C12
41. Richmond, T. G.; Crespi, A. M.; Shriver, D. F. Organometallics 1984, 3, 314-319
42. Richmond, T. G.; Shriver, D. F. Organometallics 1983, 2, 1061-1062
43. Richmond, T. G.; Shriver, D. F. Organometallics 1984, 3, 305-314
44. Michelin, R. A.; Facchin, G.; Ros, R. J. Organomet. Chem. 1985, 279, C25-C28
45. Michelin, R. A.; Ros, R.; Guadalupi, G.; Bombieri, G.; Benetollo, F.; Chapuis, G. Inorg. Chem. 1989, 28, 840-846
46. Andreassen, A. L.; Bauer, S. H. J. Chem. Phys. 1971, 56, 3802-3806
47. Michelin, R. A.; Ros., R. J. Organomet. Chem. 1979, 169, C42-C44
48. Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1978, 100, 1750-1759
49. Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc. Dalton 1976, 993-997
50. Torresan, I.; Michelin, R. A.; Marsella, A.; Zanardo, A.; Pinna, F.; Strukul, G. Organometallics 1991, 10, 623-631
51. Yoshida, T.; Matsuda, T.; Okano, T.; Kitani, T.; Otsuka, S. J. Am. Chem. Soc. 1979, 101, 2027-2038
52. Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993-999
53. Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135
54. Strukul, G.; Michelin, R. A. J. Am. Chem. Soc. 1985, 107, 7563-7568
55. Strukul, G.; Michelin, R. A.; Orbell, J. D.; Randaccio, L. Inorg. Chem. 1983, 22, 3706-3713
56. Michelin, R. A.; Strukul, G. Inorg. Chim. Acta 1979, 37, L491-L492
57. Strukul, G.; Ros, R.; Michelin, R. A. Inorg. Chem. 1982, 21, 495-500
58. Michelin, R. A.; Sgarbossa, P.; Scarso, A.; Strukul, G. Coord. Chem. Rev. 2010, 254, 646-660
59. Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidation of Organic Compounds; Academic Press: New York, 1981.
60. Mimoun, H.; Carpentier, R.; Mitschler, A.; Fischer, J.; Weiss, R. J. Am. Chem. Soc. 1980, 102, 1047-1054
61. Roussel, M.; Mimoun, H. J. Org. Chem. 1980, 45, 5387-5390
62. Igersheim, F.; Mimoun, H. Nouv. J. Chim. 1980, 4, 711-713
63. Mimoun, H. In Comprehensive Coordination Chemistry; Wilkinson, G.; Gillard, R. D.; McCleverty, J., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 6, Chapter 61.3, p 317.
64. Mimoun, H. The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York, 1983; Chapter 15, p 463.
65. Strukul, G.; Michelin, R. A. J. Chem. Soc., Chem. Commun. 1984, 1538-1539
66. Italian Pat. 1170243, 1983.
67. Strukul, G. In Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Kluwer: Dordrecht, The Netherlands, 1992; Chapter 6.
68. Sinigalia, R.; Michelin, R. A.; Pinna, F.; Strukul, G. Organometallics 1987, 6, 728-734
69. Zanardo, A.; Pinna, F.; Michelin, R. A.; Strukul, G. Inorg. Chem. 1988, 27, 1966-1973
70. Strukul, G.; Zanardo, A.; Pinna, F. Stud. Surf. Sci. Catal. 1990, 55, 81-88
71. Strukul, G.; Sinigalia, R.; Zanardo, A.; Pinna, F.; Michelin, R. A. Inorg. Chem. 1989, 28, 554-559
72. Zanardo, A.; Michelin, R. A.; Pinna, F.; Strukul, G. Inorg. Chem. 1989, 28, 1648-1653
73. Weitz, E.; Scheffer, A. Ber. Dtsch. Chem. Ges. 1921, 54, 2327-2344
74. Bunton, C. A.; Minkoff, G. J. J. Chem. Soc. 1949, 665-670
75. Helder, R.; Hummelen, J. C.; Laane, R. W. P. M; Wynberg, H. Tetrahedron Lett. 1976, 1831-1834
76. Hummelen, J. C.; Wynberg., H. Tetrahedron Lett. 1978, 1089-1092
77. Wynberg, H.; Greijdanus, B. J. Chem. Soc., Chem. Commun. 1978, 427-428
78. Wynberg, H.; Marsman, B. J. Org. Chem. 1980, 45, 158-161
79. Meijer, E. W.; Wynberg, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 975-975
80. Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organometallics 1995, 14, 1161-1167
81. Gretz, E.; Oliver, T. F.; Sen, A. J. Am. Chem. Soc. 1987, 109, 8109-8111
82. Sen, A. Acc. Chem. Res. 1988, 21, 421-428
83. Sen, A. Platinum Met. Rev. 1991, 35, 126
84. Parshall, G. W. Homogeneous Catalysis: the Application and Chemistry of Catalysis by Soluble Transition Metal Complexes; Wiley: New York, 1980; Chapter 6, pp 104-111, and Chapter 7, pp 123-129, and references therein.
85. Marsella, A.; Agapakis, S.; Pinna, F.; Strukul, G. Organometallics 1992, 11, 3578-3587
86. Michelin, R. A.; da Silva, M. F. C. G.; Pombeiro, A. J. L. Coord. Chem. Rev. 2001, 218, 75-112
87. Belluco, U.; Michelin, R. A.; Uguagliati, P.; Crociani, B. J. Organomet. Chem. 1983, 250, 565-587
88. Colladon, M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. J. Am. Chem. Soc. 2006, 128, 14006-14007
89. Colladon, M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. J. Am. Chem. Soc. 2007, 129, 7680-7689
90. Nakagawa, Y.; Kamata, K.; Kotani, M.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2005, 44, 5136-5141
91. Mizuno, N.; Nakagawa, Y.; Yamaguchi, K. J. Mol. Catal. A 2006, 251, 286-290
92. Dwars, T.; Paetzold, E.; Oehme, G. Angew. Chem., Int. Ed. 2005, 44, 7174-7199
93. Taşcioǧlu, S. Tetrahedron 1996, 52, 11113-11152
94. Engberts, J. B. F. N. Pure Appl. Chem. 1992, 64, 1653-1660
95. Lindstrom, U. M. Chem. Rev. 2002, 102, 2751-2772
96. Otto, S.; Engberts, J. B. F. N. Org. Biomol. Chem. 2003, 1, 2809-2820
97. Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209-217
98. Sinou, D.; Rabeyrin, C.; Nguefack, C. Adv. Synth. Catal. 2004, 345, 357-363
99. Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68-82
100. Sinou, D. Adv. Synth. Catal. 2002, 344, 221-237
101. Bonchio, M.; Carofiglio, T.; Di Furia, F.; Fornasier, R. J. Org. Chem. 1995, 60, 5986-5988
102. Tohma, H.; Takizawa, S.; Watanabe, H.; Fukuoka, Y.; Maegawa, T.; Kita, Y. J. Org. Chem. 1999, 64, 3519-3523
103. Scarso, A.; Strukul, G. Adv. Synth. Catal. 2005, 347, 1227-1234
104. Scarso, A.; Strukul, G. In Catalysts for Fine Chemical Synthesis: Regio- and Stereo-controlled Oxidations and Reductions; Whittal, J.; Roberts, S., Eds.; Wiley-VCH: Chichester, U.K., 2007; Vol. 5, p 297.
105. Cavarzan, A.; Bianchini, G.; Sgarbossa, P.; Lefort, L.; Gladiali, S.; Scarso, A.; Strukul, G. Chem. Eur. J. 2009, 15, 7930-7939
106. Bianchini, G; Cavarzan, A.; Scarso, A.; Strukul, G. Green Chem. 2009, 11, 1517-1520
107. Colladon, M.; Scarso, A.; Strukul, G. Adv. Synth. Catal. 2007, 349, 797-801
108. Arends, I. W. C. E. Angew. Chem., Int. Ed. 2006, 45, 6250-6252