Investigation of the thermal decomposition of [biphen(QPiPr)Pt(alk) 2]: An entry to C-C single bond activation?

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2007, Pages 944-964

  Ruhland, Klaus ^a   Brück, Andreas ^a   Herdtweck, Eberhardt ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Agostic interactions; C C activation; C H activation; Platinum; Reaction mechanisms

Indexed keywords

ACTIVATION ANALYSIS; CHLORINE COMPOUNDS; DECOMPOSITION; ETHYLENE; ISOMERIZATION; ISOMERS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM COMPOUNDS; TOLUENE;

150 ° C; AGOSTIC INTERACTIONS; BOND ACTIVATION; C-C ACTIVATIONS; C-H ACTIVATION; REACTION MECHANISM; REDUCTIVE ELIMINATION; SINGLE BOND; TRANS-CIS ISOMERIZATION; X-RAY STRUCTURE;

CHEMICAL ACTIVATION;

EID: 34250895588     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600848     Document Type: Article

References (76)

1. a) B. L. Edelbach, R. J. Lachicotte, W. D. Jones, J. Am. Chem. Soc. 1998, 120, 2843-2853;
2. b) G. Ujaque, F. Maseras, O. Eisenstein, L. Liable-Sands, A. L. Rheingold, W. Yao, R. H. Crabtree, New J. Chem. 1998, 22, 1493-1498;
3. c) Z. Lu, C. H. Jun, S. R. de Gala, M. P. Sigalas, O. Eisenstein, R. H. Crabtree, Organometallics 1995, 14, 1168-1175;
4. d) C. N. Iverson, W. D. Jones, Organometallics 2001, 20, 5745-5750;
5. e) X. Zhang, G. B. Carpenter, D. A. Sweigart, Organometallics 1999, 18, 4887-4888;
6. f) H. Schwager, S. Spyroudis, K. P. C. Vollhardt, J. Organomet. Chem. 1990, 382, 191-200;
7. g) J. J. Eisch, A. M. Piotrowski, K. I. Han, C. Krüger, Y. H. Tsay, Organometallics 1985, 4, 224-231;
8. h) R. M. Shaltout, R. Sygula, A. Sygula, F. R. Fronczek, G. G. Stanley, P. W. Rabideau, J. Am. Chem. Soc. 1998, 120, 835-836;
9. i) T. Schaub, U. Radius, Chem. Eur. J. 2005, 11, 5024-5030.
10. a) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932;
11. b) R. H. Crabtree, Chem. Rev. 1985, 85, 245-269;
12. c) J. Halpern, Inorg. Chim. Acta 1985, 100, 41-48;
13. d) G. W. Parshall, Acc. Chem. Res. 1975, 8, 113-117;
14. e) Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes (Eds.: A. E. Shilov, G. B. Shul'pin), Kluwer Academic Publishers 2000, Dordrecht, The Netherlands;
15. f) Selective Hydrocarbon Activation (Eds.: J. A. Davies, P. L. Watson, J. F. Liebman, A. Greenberg), VCH Publishers, New York/Weinheim, 1990;
16. g) Theoretical Aspects of Homogeneous Catalysis (Eds.: P. W. N. M. van Leeuwen, K. Morokuma, J. H. van Lenthe), Kluwer Academic Publishers, Dordrecht, The Netherlands, 1995;
17. h) A. D. Ryabov, Chem. Rev. 1990, 90, 403-424;
18. i) W. D. Jones, F. J. Feher, Acc. Chem. Res. 1989, 22, 91-100;
19. j) B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154-162;
20. k) B. Rybtchinski, D. Milstein, Angew. Chem. Int. Ed. 1999, 38, 870-883;
21. l) C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610-618.
22. K. Ruhland, E. Herdtweck, J. Organomet. Chem. 2005, 690, 5215-5236.
23. a) J. W. Suggs, C.-H. Jun, J. Am. Chem. Soc. 1984, 106, 3054;
24. b) J. W. Suggs, C.-H. Jun, J. Am. Chem. Soc. 1986, 108, 4679;
25. c) J. W. Suggs, C.-H. Jun, J. Chem. Soc., Chem. Commun. 1985, 92;
26. d) N. Chatani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 1999, 121, 8645;
27. e) S.-Y. Liou, M. E. van der Boom, D. Milstein, Chem. Commun. 1998, 687;
28. f) B. Rybtchinski, S. Oevers, M. Montag, A. Vigalok, H. Rozenberg, J. M. L. Martin, D. Milstein, J. Am. Chem. Soc. 2001, 123, 9064-9077;
29. g) A. Sundermann, O. Uzan, D. Milstein, J. M. L. Martin, J. Am. Chem. Soc. 2000, 122, 7095-7104;
30. h) B. Rybtchinski, D. Milstein, J. Am. Chem. Soc. 1999, 121, 4528-4529;
31. i) C.-H. Jun, C. W. Moon, D.-Y. Lee, Chem. Eur. J. 2002, 8, 2423;
32. j) C.-H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880;
33. k) C.-H. Jun, D.-Y. Lee, H. Lee, J.-B. Hong, Angew. Chem. Int. Ed. 2000, 39, 3070;
34. l) C.-H. Jun, H. Lee, S.-G. Lim, J. Am. Chem. Soc. 2001, 123, 751;
35. m) H. Salem, Y. Ben-David, L. J. W. Shimon, D. Milstein, Organometallics 2006, 25, 2292-2300.
36. Gaussian 03, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
37. a) C. A. Tolman, Chem. Rev. 1977, 77, 313;
38. b) R. Mason, D. W. Merck, Angew. Chem. 1978, 90, 195;
39. Angew. Chem. Int. Ed. Engl. 1978, 17, 183;
40. c) P. S. Pregosin, Transition Metal Nuclear Magnetic Resonance, Elsevier Science Publishers 1991, Amsterdam, The Netherlands;
41. d) C. Brevard, P. Granger, Handbook of High Resolution Multinuclear NMR, John Wiley & Sons Inc., Chichester, UK, 1981.
42. a) J. G. Verkade, L. D. Quin, Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, VCH Publishers, Weinheim, Germany, 1987;
43. b) D. W. White, J. G. Verkade, J. Magn. Reson. 1970, 3, 111-116;
44. c) M. Kainosho, A. Nakamura, Tetrahedron 1969, 25, 4071-4081.
45. a) S. Otsuka, T. Yoshida, M. Matsumoto, K. Nakatsu, J. Am. Chem. Soc. 1976, 98, 5850-5858;
46. b) A. C. Cooper, E. Clot, J. C. Huffman, W. E. Streib, F. Maseras, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1999, 121, 97-106;
47. c) G. Ujaque, A. C. Cooper, F. Maseras, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1998, 120, 361-365;
48. d) A. Cooper, W. E. Streib, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 9069-9070;
49. e) W. Baratta, E. Herdtweck, Angew. Chem. Int. Ed. 1999, 38, 1629-1631;
50. f) R. L. Harlow, D. L. Thorn, R. T. Baker, N. L. Jones, Inorg. Chem. 1992, 31, 993-997;
51. g) J. Fawcett, J. H. Holloway, G. C. Saunders, Inorg. Chim. Acta 1992, 202, 111-113;
52. h) R. Cini, A. Cavaglioni, Inorg. Chem. 1999, 38, 3751-3754;
53. i) D. Huang, W. E. Streib, J. C. Bollinger, K. G. Caulton, R. F. Winter, T. J. Scheiring, J. Am. Chem. Soc. 1999, 121, 8087-8097;
54. j) R. H. Heyn, S. A. Macgregor, T. T. Nadasdi, M. Ogasawara, O. Eisenstein, K. G. Caulton, Inorg. Chim. Acta 1997, 259, 5-26;
55. k) A. C. Albeñiz, G. Schulte, R. H. Crabtree, Organometallics 1992, 11, 242-249;
56. l) M. Brookhart, M. L. H. Green, L.-L. Wong, Prog. Inorg. Chem. 1988, 36, 1-124.
57. a) X.-L. Luo, R. H. Crabtree, J. Am. Chem. Soc. 1990, 112, 6912-6918;
58. b) E. Gutierrez-Puebla, A. Monge, M. Paneque, M. L. Poveda, S. Taboada, M. Trujillo, E. Carmona, J. Am. Chem. Soc. 1999, 121, 346-354;
59. c) W. J. Oldham, A. S. Hinkle, D. M. Heinekey, J. Am. Chem. Soc. 1997, 119, 11028-11036;
60. d) M. Saunders, L. Telkowski, M. R. Kates, J. Am. Chem. Soc. 1977, 99, 8070-8071;
61. e) R. B. Calvert, J. R. Shapley, J. Am. Chem. Soc. 1978, 100, 7726-7727;
62. f) H.-U. Siehl, Adv. Phys. Org. Chem. 1987, 23, 63-165.
63. J. Chatt, L. M. Vallarino, L. M. Venanzi, J. Chem. Soc. 1957, 2496-2505;
64. b) L. E. Crascall, J. L. Spencer, Inorg. Synth. 1990, 28, 126-135;
65. c) P. J. Buss, B. Greene, M. Orchin, Inorg. Synth. 1990, 20, 181-182.
66. a) A. L. van Geet, Anal. Chem. 1970, 42, 679-680;
67. b) H. Friebolin, G. Schilling, L. Pohl, Org. Magn. Reson. 1979, 12, 569-573;
68. c) C. Piccinni-Leopardii, O. Fabre, J. Reisse, Org. Magn. Reson. 1976, 8, 233-236;
69. d) F. H. Köhler, X. Xie, Magn. Reson. Chem. 1997, 35, 487-492;
70. e) J. Bornais, S. Brownstein, J. Magn. Reson. 1978, 29, 207-211.
71. a) Data Collection Software for Nonius κ-CCD devices, Delft (The Netherlands), 2001;
72. b) Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307;
73. c) SIR92: A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435-436;
74. d) International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2 (Ed.: A. J. C. Wilson), Kluwer Academic Publishers, Dordrecht (The Netherlands), 1992;
75. e) A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2001;
76. f) G. M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1998.