Synthesis, characterization, and reaction chemistry of PtCl2[P(m-C6H4 SO3Na)3]2, an alkyne hydration catalyst

Organometallics

Volumn 20, Issue 20, 2001, Pages 4237-4245

  Francisco, Laura W ^a,b   Moreno, Debra A ^a   Atwood, Jim D ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b D'YOUVILLE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE HYDRATION CATALYSTS; ALLYLIC SUBSTITUTION; HYDROFORMYLATION; MARKOVNIKOV HYDRATION; REACTION CHEMISTRY;

COMPLEXATION; HYDRATION; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PH EFFECTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PLATINUM COMPOUNDS;

EID: 0035497161     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0104870     Document Type: Article

References (111)

1. (a) Breslow, R. Water as a Solvent for Chemical Reactions. Green Chemistry; Oxford Press: London, 1998; pp 225-233.
2. (b) Li, C.-J. Water as a Benign Solvent for Chemical Syntheses. Green Chemistry; Oxford Press: London, 1998; pp 234-249.
3. (a) Lippert, B. Coord. Chem. Rev. 1999, 182, 263-295.
4. (b) Trovó, G.; Longato, B.; Corain, B.; Tapparo, A.; Furlani, A.; Scarcia, V.; Baccichetti, F.; Bordin, F.; Palumbo, M. J. Chem. Soc., Dalton Trans. 1993, 1547-1550.
5. (a) Hanson, B. E. Coord. Chem. Rev. 1999, 185/186, 795-807.
6. (b) Herrmann, W. A.; Kohlpainter, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
7. (c) Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177-186.
8. (d) Kalck, P.; Monteil, F. Adv. Organomet. Chem. 1992, 34, 219-283.
9. (e) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9-17.
10. (f) Papadagianakis, G.; Sheldon, R. A. New J. Chem. 1996, 20, 175.
11. (g) Roundhill, D. M. Adv. Organomet. Chem. 1995, 38, 172.
12. (h) Darensbourg, D. J.; Joó, F.; Kannisto, M.; Reibenspies, J. H.; Dagle, D. J. Inorg. Chem. 1994, 33, 200.
13. Deshpande, R. M.; Purwanto; Delmas, H.; Chaudhari, R. V. Ind. Eng. Chem. Res. 1996, 35, 3927-3933.
14. (a) Borowski, A. F.; Cole-Hamilton, D. J.; Wilkinson, G. Nouv. J. Chim. 1978, 2, 137-144.
15. (b) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem. Soc., Chem. Commun. 1991, 1684-1685.
16. (c) Amrani, Y.; Lecomte, L.; Sinou, D.; Bakos, J.; Toth, I.; Heil, B. Organometallics 1989, 8, 542-547.
17. (a) Amatore, C.; Blart, E.; Genêt, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829-6839.
18. (b) Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.
19. (a) dos Santos, S.; Tong, Y.; Quignard, F.; Choplin, A.; Sinou, D.; Dutasta, J. P. Organometallics 1998, 17, 78-89.
20. (b) Safi, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025-2028.
21. (a) Henry, P. M. Acc. Chem. Res. 1973, 6, 16-24.
22. (b) Francis, J. W.; Henry, P. M. Organometallics 1991, 10, 3498-3503.
23. (c) McGrath, D. V.; Grubbs, R. H. Organometallics 1994, 13, 224-235.
24. (d) Francis, J. W.; Henry, P. M. Organometallics 1992, 11, 2832-2836.
25. (a) Kiji, J.; Okano, T.; Nishiumi, W.; Konishi, H. Chem. Lett. 1988, 957-960.
26. (b) Monteil, F.; Kalck, P. J. Organomet. Chem. 1994, 482, 45-51.
27. (c) Stille, J. K.; James, D. E.; Hines, L. F. J. Am. Chem. Soc. 1973, 95, 5062-5064.
28. (a) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791.
29. (b) Hamed, O.; Henry, P. M. Organometallics 1998, 17, 5184-5189.
30. (c) Zaw, K.; Lautens, M.; Henry, P. M. Organometallics 1985, 4, 1286-1291.
31. (a) Stunnenberg, F.; Niele, F. G. M.; Drent, E. Inorg. Chim. Acta 1994, 222, 225-233.
32. (b) ten Brink, G. J.; Arends, I.; Papadogianakis, G.; Sheldon, R. A. Appl. Catal. A: Gen. 2000, 194/195, 435-442.
33. (c) Stille, J. K.; James, D. E. J. Am. Chem. Soc. 1975, 97, 674-676.
34. (d) Bäckvall, J. E.; Åkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411-2416.
35. (e) Hamed, O.; Thompson, C.; Henry, P. M. J. Org. Chem. 1997, 62, 7082-7083.
36. (f) Hamed, O.; Henry, P. M. Organometallics 1997, 16, 4903-4909.
37. (g) Strukul, G.; Michelin, R. A. J. Chem. Soc., Chem. Commun. 1984, 1538-1539.
38. (h) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310-8311.
39. (i) ten Brink, G. J.; Arends, I.; Sheldon, R. A. Science 2000, 287, 1636-1639.
40. (a) Ganguly, S.; Roundhill, D. M. J. Chem. Soc., Chem. Commun. 1991, 639-640.
41. (b) Ganguly, S.; Roundhill, D. M. Organometallics 1993, 12, 4825-4832.
42. (c) Atkins, K. E.; Walker, W. E.; Manyik, R. M. J. Chem. Soc., Chem. Commun. 1971, 330.
43. (d) Yoshida, T.; Matsuda, T.; Okano, T.; Kitani, T.; Otsuka, S. J. Am. Chem. Soc. 1979, 101, 2027-2038.
44. (e) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345-3346.
45. (f) Bennett, M. A.; Jin, H.; Li, S.; Rendina, L. M.; Willis, A. C. J. Am. Chem. Soc. 1995, 117, 8335-8340.
46. (g) Inoue, Y.; Sato, M.; Satake, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1983, 56, 637-638.
47. (h) Döbler, C.; Mehltretter, G.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 3026-3028.
48. Jensen, C. M.; Trogler, W. C. Science 1986, 233, 1069-1070.
49. (a) Ramprasad, D.; Yue, H. J.; Marsella, J. A. Inorg. Chem. 1988, 27, 3151-3155.
50. (b) Grushin, V. V.; Akhrem, I. S.; Vol'pin, M. E. J. Organomet. Chem. 1989, 371, 403-419.
51. (a) Maruoka, K.; Sano, H.; Shinoda, K.; Yamamoto, H. Chem. Lett. 1987, 73-76.
52. (b) Zweifel, G.; Brown, H. C. Org. React. 1963, 13, 2-19.
53. (a) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723-729.
54. (b) Yoshida, T.; Matsuda, T.; Okano, T.; Kitani, T.; Otsuka, S. J. Am. Chem. Soc. 1979, 101, 2027.
55. (c) Shibata, A.; Yamaguchi, T.; Ito, T. Inorg. Chim. Acta 1997, 265, 197-204.
56. (d) Gracia-Mora, J.; Díaz, D. Transition Met. Chem. 1998, 23, 57-61.
57. (e) Kaminskaia, N. V.; Guzei, I. A.; Kostíc, N. M. J. Chem. Soc., Dalton Trans. 1998, 3879-3885.
58. (f) Kaminskaia, N. V.; Kostíc, N. M. J. Chem. Soc., Dalton Trans. 1996, 3677-3686.
59. (g) Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618-3622.
60. Meier, I. K.; Marsella, J. A. J. Mol. Catal. 1993, 78, 31-42.
61. (a) Khan, M. M. T.; Halligudi, S. B.; Shukla, S. J. Mol. Catal. 1990, 58, 299-305.
62. (b) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1998, 37, 2867-2869.
63. Blum, J.; Huminer, H.; Alper, H. J. Mol. Catal. 1992, 75, 152-160.
64. Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127-3130.
65. Strukul, G.; Varagnolo, A.; Pinna, F. J. Mol. Catal. A 1997, 117, 413-423.
66. (a) Jennings, P. W.; Hartman, J. W.; Hiscox, W. C. Inorg. Chim. Acta 1994, 222, 317-322.
67. (b) Hartman, J. W.; Hiscox, W. C.; Jennings, P. W. J. Org. Chem. 1993, 58, 7613-7614.
68. (c) Hiscox, W.; Jennings, P. W. Organometallics 1990, 9, 1997-1999.
69. (d) Baidossi, W.; Lahav, M.; Blum, J. J. Org. Chem. 1997, 62, 669-672.
70. Chatt, J.; Wilkins, R. G. J. Chem. Soc. 1951, 2532.
71. Gillard, R. D.; Pilbrow, M. F. J. Chem. Soc., Dalton Trans. 1974, 2320.
72. Pidcock, A.; Richards, R. E.; Venanzi, L. M. Proc. Chem. Soc. London 1962, 184.
73. Gillard, R. D.; Pilbrow, M. E. J. Chem. Soc., Dalton Trans. 1974, 2320-2325.
74. Jensen, K. A. Z. Anorg. Chem. 1936, 229, 236.
75. Malatesta, L.; Cariello, C. J. Chem. Soc. 1958, 2323.
76. (a) Tayim, H. A.; Bouldoukian, A.; Awad, F. J. Inorg. Nucl. Chem. 1970, 32, 3799.
77. (b) Winzer, A.; Born, E. Z. Chem. 1970, 10, 438.
78. Hsu, C. Y.; Leshner, B. T.; Orchin, M. Inorg. Synth. 1979, 15, 114-115.
79. (a) Larpent, C.; Patin, H. Appl. Organomet. Chem. 1987, 1, 529-534.
80. (b) Herrmann, W. A.; Kellner, J.; Riepl, H. J. Organomet. Chem. 1990, 389, 103-128.
81. Kerr, G. T.; Schweizer, A. E. Inorg. Synth. 1980, 20, 48-49.
82. 34
83. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy; Oxford University Press: London, 1987; pp 217-218.
84. Basolo, F.; Chatt, J.; Gray, H. B.; Pearson, R. G.; Shaw, B. L. J. Chem. Soc. 1961, 2207.
85. (a) Papadogianakis, G.; Peters, J. A.; Maat, L.; Sheldon, R. A. J. Chem. Soc., Chem. Commun. 1995, 21, 1105-1106.
86. (b) Favez, R.; Roulet, R.; Pinkerton, A. A.; Schwarzenbach, D. Inorg. Chem. 1980, 19, 1356-1365.
87. Hollis, L. S.; Lippard, S. J. J. Am. Chem. Soc. 1983, 105, 3494-3503.
88. (a) Pregosin, P. S. Transition Metal Nuclear Magnetic Resonance; New York: 1991; pp 216-263.
89. (b) Goggin, P. L.; Goodfellow, R. J.; Haddock, S. R.; Taylor, B. F.; Marshall, R. H. J. Chem. Soc., Dalton Trans. 1976, 459-467.
90. (c) Georgii, I.; Mann, B. E.; Taylor, B. F.; Musco, A. Inorg. Chim. Acta 1984, 86, L81-L82.
91. (d) Caseri, W.; Pregosin, P. S. Organometallics 1988, 7, 1373-1380.
92. (a) Kuntz, E. G.; Vittori, O. M. J. Mol. Catal. A: Chem. 1998, 129, 159-171.
93. (b) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901.
94. (c) McLaughlin, P. A.; Verkade, J. G. Organometallics 1998, 17, 5937-5940.
95. (d) dos Santos, S.; Tong, Y.; Quignard, F.; Choplin, A.; Sinou, D.; Dutasta, J. P. Organometallics 1998, 17, 78-89.
96. Bushnell, G. W.; Dixon, K. R.; Hunter, R. G.; McFarland, J. J. Can J. Chem. 1972, 50, 3694.
97. Wimmer, S.; Castan, P.; Wimmer, F. L.; Johnson, N. P. J. Chem. Soc., Dalton Trans. 1989, 403.
98. (a) Li, J. J.; Li, W.; Sharp, P. R. Inorg. Chem. 1996, 35, 604.
99. (b) Li, J. J.; Li, W.; James, A. J.; Holbert, T.; Sharp, T. P.; Sharp, P. R. Inorg. Chem. 1999, 38, 1563.
100. Miyamoto, T.; Suzuki, Y.; Ichida, H. Bull. Chem. Soc. Jpn. 1992, 65, 3386.
101. Boreham, C. J.; Broomhead, J. A.; Fairlie, D. P. Aust. J. Chem. 1981, 34, 659.
102. Gill, D. S.; Rosenbert, B. J. Am. Chem. Soc. 1982, 104, 4598.
103. Bielli, E.; Gidney, P. M.; Gillard, R. D.; Heaton, B. T. J. Chem. Soc., Dalton Trans. 1974, 2133.
104. 13C NMR of Transition Metal Phosphine Complexes; Springer-Verlag: Berlin, 1979; pp 42-45.
105. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
106. Utimoto, K. Pure Appl. Chem. 1983, 55, 1845.
107. Davies, G. R.; Hewertson, W.; Mais, R. H. B.; Owston, P. G.; Patel, C. G. J. Chem. Soc. A 1970, 1873.
108. Davies, B. W.; Payne, N. C. Can. J. Chem. 1973, 51, 3477.
109. Gerisch, M.; Heinemann, F. W.; Bögel, H.; Steinborn, D. J. Organomet. Chem. 1997, 548, 247.
110. Herrmann, W. A.; Kohlpainter, C. W. Inorg. Synth. 1998, 32, 14.
111. Hollis, L. S.; Lippard, S. J. J. Am. Chem. Soc. 1983, 105, 3494-3503.