Dendrimer-phosphine complexes with platinum(0) at the core

Organometallics

Volumn 20, Issue 25, 2001, Pages 5342-5350

  Balaji, B S ^a   Obora, Yasushi ^a   Ohara, Daisuke ^a   Koide, Shigehiro ^a   Tsuji, Yasushi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIDENTATE LIGANDS; DENDRIMER; MONODENTATE LIGANDS; PHOSPHINE;

COMPLEXATION; MACROMOLECULES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PLATINUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 0035843054     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010687b     Document Type: Article

References (118)

1. (a) Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 155.
2. (b) Denkewalter, R. G.; Kolc, J. F. Lukasavage, U.S. Pat. 4189872, 1981 [Chem. Abstr. 1985, 102, P79324q].
3. (c) Tomalia, D. A.; Baker, H.; Dewald, J. R.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117.
4. (d) Newkome, G. R.; Yao, Z. Q.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003.
5. (a) Wörner, C.; Mülhaupt, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1306.
6. (b) De Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1308.
7. (c) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
8. (d) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482.
9. Launay, N.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1995, 117, 3282.
10. (a) Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
11. (b) Miller, T. M.; Neenan, T. X. Chem. Mater. 1990, 2, 346.
12. (c) Moore, J. S.; Xu, Z. Macromolecules 1991, 24, 5893.
13. (d) Uhrich, K. E.; Fréchet, J. M. J. J. Am. Chem. Soc., Perkin Trans. 1 1992, 1623.
14. (e) Kawaguchi, T.; Walker, K. L.; Moore, J. S. J. Am. Chem. Soc. 1995, 17, 2159.
15. (f) Jayaraman, M.; Fréchet, J. M. J. J. Am. Chem. Soc. 1998, 120, 12996.
16. (a) Fréchet, J. M. J. Science 1994, 263, 1710.
17. (b) Hawker, C. J.; Malmströrm, E. E.; Frank, C. W.; Kampf, J. P. J. Am. Chem. Soc. 1997, 119, 9903.
18. (c) Miller, T. M.; Neenan, T. X.; Zayas, R.; Bair, H. E. J. Am. Chem. Soc. 1992, 114, 1018.
19. (d) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. Polymer 1994, 35, 4489.
20. (e) Jiang, D. L.; Aida, T. J. Am. Chem. Soc. 1998, 120, 10895.
21. (f) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665.
22. (g) Majoral, J. P.; Caminade, A. M. Chem. Rev. 1999, 99, 845.
23. Hecht, S.; Frechet, J. M. J. Angew. Chem., Int. Ed. Engl. 2001, 40, 74, and references therein.
24. (a) Jansen, J. F. G. A.; De Brabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226.
25. (b) Seebach, D.; Lapierre, J. M.; Skobridis, K.; Greiveldinger, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 440.
26. Ottaviani, M. F.; Cossu, E.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1995, 117, 4387.
27. (a) Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
28. (b) Kriesel, J. W.; Konig, S.; Freitas, M. A.; Marshall, A. G.; Leary, J. A.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 12207, and references therein.
29. (a) Maraval, V.; Laurent, R.; Caminade, A. M.; Majoral, J. P. Organometallics 2000, 19, 4025.
30. (b) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem. Int., Ed. Engl. 2000, 39, 176.
31. (c) Vögtle, F.; Plevoets, M.; Nieger, M.; Azzellini, G. C.; Credi, A.; De Cola, L.; De Marchis, V.; Venturi, M.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 6290.
32. (d) Dandliker, P. J.; Diederich, F.; Gross, M.; Knobler, C. B.; Louati, A.; Sanford, E. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1739.
33. (e) Bhyrappa, P.; Young, J. K.; Moore, J. S.; Suslick, K. S. J. Am. Chem. Soc. 1996, 118, 5078.
34. (f) Chow, H. F.; Mak, C. C. J. Org. Chem. 1997, 62, 5116.
35. Larre, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Chem. Eur. J. 1998, 10, 2031.
36. (a) Feeder, N.; Geng, J.; Goh, P. G.; Johnson, B. F. G.; Martin, C. M.; Shepard, D. S.; Zhou, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 1661.
37. (b) Eggeling, E. B.; Hovestad, N. J.; Jastrzebski, J. T. B. H.; Vogt, D.; van Koten, G. J. Org. Chem. 2000, 65, 8857.
38. (c) Beletskaya, I. P.; Chuchurjukin, A. V.; Dijkstra, H. P.; van Klink, G. P. M.; van Koten, G. Tetrahedron Lett. 2000, 41, 1081.
39. (d) Arya, P.; Rao, N. V.; Singkhonrat, J.; Alper, H.; Bourque, S. C.; Manzer, L. E. J. Org. Chem. 2000, 65, 1881.
40. (e) Bourque, S. c.; Maltais, F.; Xiao, W-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035.
41. (f) Gong, A.; Fan, Q.; Chen, Y.; Liu, H.; Chen, C.; Xi, F. J. Mol. Catal. A: Chem. 2000, 159, 225.
42. (g) Murfee, H. J.; Thoms, T. P. S.; Greaves, J.; Hong, B. Inorg. Chem. 2000, 39, 5209.
43. (h) Achar, S.; Puddephatt, R. J. Organometallics 1995, 14, 1681.
44. (i) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211.
45. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Application of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; Chapter 10.
46. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994; Chapter 2.
47. (a) Frohning, C. D.; Kohlpainter, C. W. In Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, Germany, 1996; p 1.
48. (b) Trzeciak, A. M.; Ziolkowski, J. J. Coord. Chem. Rev. 1999, 190-192, 883.
49. (a) Tsuji, J. Palladium Reagents and Catalysts; John Wiley and Sons: Chichester, U.K., 1995.
50. (b) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 797.
51. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355;
52. Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
53. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
54. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
55. (f) Tsuji, J. Pure Appl. Chem. 1980, 54, 197;
56. Tsuji, J. Pure Appl. Chem. 1980, 58, 869.
57. (g) Tsuji, J. Tetrahedron 1986, 42, 4361.
58. Catalano, V. J. and Parodi, N. Inorg. Chem. 1997, 36, 537.
59. Engel, R.; Rengan, K.; Chan, C. S. Heteroat. Chem. 1993, 4, 181.
60. Pignolet, L. H. Homogeneous Catalysis with Metal Phosphine Complexes; Plenum: New York, 1983.
61. (a) Fritzsche, H.; Hasserodt, U.; Korte, F. Chem. Ber. 1965, 98, 171.
62. (b) Huck, W. T. S.; Snellink-Ruël van Veggel, F. C. J. M.; Reinhoudt, D. N. Organometallics 1997, 16, 4287.
63. Mirabelli, C. K.; Hill, D. T.; Faucette, L. F.; McCabe, F. L.; Girard, G. R.; Bryan, D. B.; Sutton, B. M.; Bartus, J. o.; Crooke, S. T.; Jhonson, R. K. J. Med. Chem. 1987, 30, 2181.
64. (a) Belluco, U. In Organometallic and Coordination Chemistry of Platinum; Maitlis, P. M., Stone, F. G. A., West, R., Eds.; Academic: New York, 1974; p 485.
65. (b) Anderson, G. K. In Comprehensive Organometallic Chemistry II: Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 9, p 431.
66. Asker, K. A.; Hitchcock, P. B.; Moulding, R. P.; Seddon, K. R. Inorg. Chem. 1990, 29, 4146.
67. Farkas, E.; Kollár, L.; Moret, M.; Sironi, A. Organometallics 1996, 15, 1345.
68. 6) of the trans isomer appeared at δ 22.08 ppm and the cis isomer at 31.07 ppm, which are very close to the corresponding TPP analogues.
69. (b) Yang, Z.; Han, X.; Li, T.; Song, Y. Ke Xue Tong Bao 1985, 841.
70. (a) Mason, M. R.; Verkade, J. G. Organometallics 1992, 11, 2212.
71. (b) Ioele, M.; Ortaggi, G.; Scarsella, M.; Sleiter, G. Polyhedron 1991, 10, 2475.
72. (c) Malatesta, L.; Cariello, C. J. Chem. Soc. 1958, 2323.
73. Sen, A.; Halpern, J. Inorg. Chem. 1980, 19, 1073.
74. (a) Ugo, R.; Cariati, F.; Monica, G. L. Inorg. Synth. 1990, 28, 123.
75. (b) Grushin, V. V.; Akhrem, I. S.; Vol'pin, M. E. J. Organomet. Chem. 1989, 371, 403.
76. (a) Darensbourg, D. J.; Decuir, T. J.; Stafford, N. W.; Robertson, J. B.; Draper, J. D.; Reibenspies, J. H.; Kathó, A. Joó, F. Inorg. Chem. 1997, 36, 4218.
77. (b) Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Chem. Soc. 1976, 98, 5850.
78. (c) Tolman, C. A.; Seidel, W. C.; Gerlach, D. H. J. Am. Chem. Soc. 1972, 94, 2669.
79. (a) Martelli, M.; Pilloni, G.; Zotti, G.; Daolio, S. Inorg. Chim. Acta 1974, 11, 155.
80. (b) Engelhardt, L. M.; Patrick, J. M.; Raston, C. L.; Twiss, P.; White, A. H. Aust. J. Chem. 1984, 37, 2193.
81. (a) Yamamoto, A. Organotransition Metal Chemistry; John Wiley and Sons: New York, 1986; p 195.
82. (b) Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; John Wiley and Sons: New York, 1986; Chapter 6.
83. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Application of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 246.
84. (a) Pearson, R. G.; Figdore, P. E. J. Am. Chem. Soc. 1980, 102, 1541.
85. (b) Kawata, N.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1974, 47, 1807.
86. Davies, J. A.; Eagle, C. T.; Otis, D. E.; Venkataraman, U. Organometallics 1989, 8, 1080.
87. Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828.
88. (a) Goodman, J. M. Chemical Application of Molecular Modeling; Royal Society of Chemistry: Cambridge, 1998.
89. (b) Smith, W. B. Introduction to Theoretical Organic Chemistry and Molecular Modeling; John Wiley and Sons: New York, 1996.
90. (c) Young, D. C. Computational Chemistry; John Wiley and Sons: New York, 2001.
91. (d) Grant, G. H.; Richards, W. G. Computational Chemistry; Oxford University: Oxford, U.K., 1995.
92. (a) Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian: Pittsburgh, PA, 1996.
93. (b) Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley and Sons: New York, 1986.
94. Segal, G. A. Semiempirical Methods of Electronic Structure Calculation; Plenum: New York, 1977.
95. Rappé, A. K.; Casewit, C. J. Molecular Mechanics across Chemistry; University Science Books: Sausalito, CA, 1997.
96. (a) Goto, H. J. Am. Chem. Soc. 1989, 111, 8950.
97. (b) Goto, H.; Osawa, E. J. Chem. Soc., Perkin Trans. 2 1993, 187.
98. (a) Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566.
99. (b) Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
100. 36b and this initial structure was optimized by the DFT calculation.
101. (b) Merwin, R. K.; Schnabel, R. C.; Koola, J. D.; Roddick, D. M. Organometallics 1992, 11, 2972.
102. (a) Parr, R. G.; Tang, W. Density-Functional Theory of Atoms and Molecules; Oxford University: Oxford, U.K., 1989.
103. (b) Labanowski, J. K.; Andzelm, J. W. Density Functional Methods in Chemistry; Springer: New York, 1991.
104. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
105. (a) Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III., Ed.; Plenum: New York, 1976; Vol. 3, p 1.
106. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
107. (c) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
108. (d) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
109. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
110. (b) Stewart, J. J. P. Comput. Chem. 1989, 10, 221.
111. (a) Fruchtl, H. A.; Nobes, R. H.; Bliznyuk, A. THEOCHEM 2000, 506, 87.
112. (b) Greatbanks, S. P.; Gready, J. E.; Limaye, A. C.; Rendell, A. P. J. Comput. Chem. 2000, 21, 788.
113. (c) Titmuss, S. J.; Cummins, P. L.; Bliznyuk, A.; Rendell, A. P.; Gredy, J. E. Chem. Phys. Lett. 2000, 320, 169.
114. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed.; Burrerworth-Heinemann: Oxford, U.K., 1997.
115. Senear, A. E.; Valient, W.; Wirth, J. J. Org. Chem. 1960, 25, 2001.
116. Drew, D.; Doyle, J. R. Inorg. Synth. 1972, 13, 48.
117. It is well-known that some DPPE complexes of Pt retain a small amount of solvent of crystallization, which cannot be removed even by prolonged evacuation. Appleton, T. G.; Bennett, M. A. Inorg. Chem. 1978, 17, 738.
118. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.