"Synergistic effects of two Si-H groups and a metal center" in transition metal-catalyzed hydrosilylation of unsaturated molecules: A mechanistic study of the RhCl(PPh3)3-catalyzed hydrosilylation of ketones with 1,2-bis(dimethylsilyl)benzene

Organometallics

Volumn 27, Issue 14, 2008, Pages 3502-3513

  Sunada, Yusuke ^a   Fujimura, Yoshiki ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; HYDROSILYLATION; RHODIUM COMPOUNDS; SILICON; TRANSITION METALS;

IN TRANSITIONS; MECHANISTIC STUDIES; METAL CENTERS; SYNERGISTIC EFFECTS; UNSATURATED MOLECULES;

METALS;

EID: 49349098955     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800151w     Document Type: Article

References (96)

1. (a) Ojima, I. In The Chemistry of Organosilicon Compounds; Patai, S., Rapport, Z., Eds.; Wiley: New York, 1989.
2. (b) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley: New York, 2000.
3. (c) Speier, J. L. Adv. Organomet. Chem. 1979, 17, 407.
4. (d) Comprehensive Handbook on Hydrosilylation; Marciniec, B., Ed.; Pergamon: Oxford, U.K., 1992.
5. (e) Marciniec, B.; Guliński, J. J. Organomet. Chem. 1993, 446, 15.
6. (f) Marciniec, B. Silicon Chem. 2002, 7, 155.
7. (a) Ojima, I.; Hirai, K. Asymmetric Synthesis; Academic Press: New York, 1985.
8. (b) Nishiyama, H.; Itoh, K. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000.
9. (c) Hayashi, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
10. (a) Spier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1957, 79, 974.
11. (b) Hitchcock, P. B.; Lappert, M. F.; Warhurst, N.-J. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 438.
12. (c) Lappert, M. F.; Maskell, R. K. J. Organomet. Chem. 1984, 264, 217.
13. (d) Tsuji, J.; Hara, M.; Ohno, K. Tetrahedron 1974, 30, 2143.
14. (e) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
15. (f) Kumada, M.; Kiso, Y.; Umeno, M. J. Chem. Soc., Chem. Commun. 1970, 611.
16. (g) Ojima, I.; Fuchikami, T.; Yatabe, M. J. Organomet. Chem. 1984, 260, 335.
17. (h) Marciniec, B.; Urbaniak, W.; Pawlak, P. J. Mol. Catal. 1982, 74, 323.
18. (i) Chalk, A. J. J. Organomet. Chem. 1970, 27, 207.
19. (j) Dumont, W.; Poulin, J.-C.; Dang, T.-P.; Kagan, H. B. J. Am. Chem. Soc. 1978, 25, 8295.
20. (k) Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1974, 25, 8295.
21. (l) Brunner, H. Synthesis 1988, 645.
22. (m) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
23. (n) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989.
24. (o) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
25. (p) Evans, D. A.; Michael, F. E.; Tedrow, J. S.; Campos, K. R. J. Am. Chem. Soc. 2003, 125, 3534.
26. (q) Ojima, I.; Kogure, T.; Kumagai, M. J. Org. Chem. 1977, 42, 1671.
27. Corriu, R. J. P.; Moreau, J. J. E.; Pataud-Sat, M. J. Organomet. Chem. 1982, 228, 301.
28. (a) Nagashima, H.; Tatebe, K.; Ishibashi, I.; Sakakibara, J.; Itoh, K. Organometallics 1989, 8, 2495.
29. (b) Nagashima, H.; Tatebe, K.; Itoh, K. J. Chem. Soc., Perkin Trans. 1 1989, 1707.
30. (c) Nagashima, H.; Tatebe, K.; Ishibashi, I.; Nakaoka, A.; Sakakibara, J.; Itoh, K. Organometallics 1995, 14, 2868.
31. (a) Hanada, S.; Ishida, T.; Motoyama, Y.; Nagashima, H. J. Org. Chem. 2007, 72, 7551.
32. (b) Hanada, S.; Motoyama, Y.; Nagashima, H. Tetrahedron Lett. 2006, 47, 6173.
33. (c) Motoyama, Y.; Mitsui, K.; Ishida, T.; Nagashima, H. J. Am. Chem. Soc. 2005, 127, 13150.
34. (a) Uchimaru, Y.; Lautenschlager, H.-J.; Wynd, A. J.; Tanaka, M.; Goto, M. Organometallics 1992, 11, 2639.
35. (b) Tanaka, M.; Uchimaru, Y.; Lautenschlager, H.-J. Organometallics 1991, 10, 16.
36. (c) Tanaka, M.; Uchimaru, Y.; Lautenschlager, H.-J. Chem. Lett. 1992, 45.
37. (d) Tanaka, M.; Uchimaru, Y.; Lautenschlager, H.-J J. Organomet. Chem. 1992, 428, 1.
38. Uchimaru, Y.; El Sayed, A. M. M.; Tanaka, M. Organometallics 1993, 12, 2065.
39. (a) Curtis, M. A.; Green, J. J. Am. Chem. Soc. 1978, 100, 6362.
40. (b) Green, J.; Curtis, M. A. J. Am. Chem. Soc. 1977, 99, 5176.
41. (c) Curtis, M. A.; Green, J.; Butler, W. M. J. Organomet. Chem. 1979, 164, 371.
42. (a) Muir, K. W.; Ibers, J. A. Inorg. Chem. 1970, 9, 440.
43. (b) de Charentenay, F.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1968, 787.
44. (c) Haszeldine, R. N.; Parish, R. V.; Taylor, R. J. J. Chem. Soc. A 1974, 2577.
45. (d) Haszeldine, R. N.; Parish, R. V.; Parry, D. J. Chem. Soc. A 1969, 683.
46. gNMR Wer. 4.0; Cherwell Scientific Ltd.: Oxford, United Kingdom, 1995.
47. (a) Nishihara, Y.; Takemura, M.; Osakada, K. Organometallics 2002, 21, 825.
48. (b) Osakada, K.; Koizumi, T.; Yamamoto, T. Organometallics 1997, 16, 2063.
49. (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
50. (b) Schubert, U. Adv. Organomet. Chem. 1990, 30, 151.
51. (a) Schubert, U.; Gilges, H. Organometallics 1996, 15, 2373.
52. (b) Nikolov, G. I. Adv. Organomet. Chem. 2005, 53, 217.
53. Taw, F. L.; Bergman, R. G.; Brookhart, M. Organometallics 2004, 23, 886.
54. Mitchell, G. P.; Tilley, T. D. Organometallics 1996, 15, 3477.
55. Loza, M.; Faller, J. W.; Crabtree, R. H. Inorg. Chem. 1995, 34, 2937.
56. (a) Barton, T. J.; Jacobi, S. A. J. Am. Chem. Soc. 1980, 102, 7979.
57. (b) Eaborn, C.; Safa, K. D. J. Organomet. Chem. 1981, 2042, 169.
58. (c) Doszczak, L.; Fey, P.; Tacke, R. Synlett 2007, 5, 753.
59. (d) Doszczak, L.; Tacke, R. Organometallics 2007, 26, 5722.
60. Dehydrogenative double oxidative addition of 1,2-disilylbenzenes and other bifunctional silanes are well-established:(a) Shimada, S.; Tanaka, M. Coord. Chem. Rev. 2006, 250, 991.
61. (b) Shimada, S.; Tanaka, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1856.
62. (c) Shimada, S.; Rao, M. L. N.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2001, 40, 213.
63. (d) Shimada, S.; Li, Y.-H.; Rao, M. L. N.; Tanaka, M. Organometallics 2006, 25, 3796.
64. (e) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289.
65. (f) Shimada, S.; Rao, M. L. N.; Li, Y.-H.; Tanaka, M. Organometallics 2005, 24, 6029.
66. (g) Shimada, S.; Rao, M. L. N.; Tanaka, M. Organometallics 1999, 18, 291.
67. (h) Chen, W.; Shimada, S.; Tanaka, M. Science 2002, 295, 308.
68. (i) Bourg, S.; Boury, B.; Carré, F. H.; Corriu, R. J. P. Organometallics 1998, 17, 167.
69. (j) Lee, Y.-J.; Lee, J. -D.; Kim, S. -J.; Ko, J.; Suh, I. -H.; Cheong, M.; Kang, S. O. Organometallics 2004, 23, 135.
70. (k) Pfeiffer, J.; Kickelbick, G.; Schubert, U. Organometallics 2000, 19, 62.
71. (l) Kang, Y.; Kim, K.; Kang, S.-O.; Ko, J.; Heaton, B. T.; Barkley, J. V. J. Organomet. Chem. 1997, 55-2, 79.
72. (m) Loza, M. L.; de Gala, S. R.; Crabtree, R. H. Inorg. Chem. 1994, 33, 5073.
73. (n) Fink, W. Helv. Chem. Acta 1976, 59, 606.
74. (o) Fink, W. Helv. Chem. Acta 1974, 57, 1010.
75. (p) Fink, W. Helv. Chem. Acta 1975, 58, 1464.
76. (q) Corriu, R. J. P.; Moreau, J. J. E.; Pataund-Sat, M. J. Org. Chem. 1981, 46, 3372.
77. (r) Corriu, R. J. P.; Moreau, J. J. E.; Pataund-Sat, M. J. Organometallics 1985, 4, 623.
78. 2 was reported: Dioumaev, V. K.; Yoo, B. R.; Procopio, L. J.; Carroll, P. J.; Berry, D. H. J. Am. Chem. Soc. 2003, 125, 8936.
79. Chelate-assisted triple oxidative addition of three Si-H moieties was reported:(a) Djurovich, P. I.; Safir, A. L.; Keder, N. L.; Watts, R. J. Inorg. Chem. 1992, 31, 3195.
80. (b) Chen, W.; Shimada, S.; Hayashi, T.; Tanaka, M. Chem. Lett. 2001, 1096.
81. (c) Chen, W.; Shimada, S.; Tanaka, M.; Kobayashi, Y.; Saigo, K. J. Am. Chem. Soc. 2004, 126, 8072.
82. 2-(H- Si) moiety:(a) Delpech, F.; Sabo-Etienne, S.; Daran, J.-C.; Chaudret, B.; Hussein, K.; Marsden, C. J.; Barfhelat, J. -C. J. Am. Chem. Soc. 1999, 121, 6668.
83. (b) Delpech, F.; Sabo-Etienne, S.; Chaudret, B.; Daran, J.-C. J. Am. Chem. Soc. 1999, 121, 6668.
84. (c) Schubert, U.; Gruben, S. Monatsh. Chem. 1998, 129, 437.
85. (a) Ison, E. A.; Corbin, R. A.; Abu-Omar, M. M. J. Am. Chem. Soc. 2005, 127, 11938.
86. (b) Field, L. D.; Messerle, B. A.; Rehr, M.; Soler, L. P.; Hambley, T. W. Organometallics 2003, 22, 2387.
87. One of the reviewers suggested the possibility of disilaindane 6 as intermediate species to form the methyl migrated product 5. This is excluded by the RhCl(PPh3)3-catalyzed hydrosilylation of acetone with 1,2-bis(di- methylsilyl)benzene in the presence of disilaindane 6, in which 6 was proved to be inert toward the reaction with acetone under the conditions.
88. Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. A. 1966, 1711.
89. (b) Osborn, J. A.; Wilkinson, G. Inorg. Synth. 1967, 10, 67.
90. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F. Inorg. Synth. 1974, 15, 58.
91. (a) Sheldrick, G. M. SHELX97; 1997.
92. (b) Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Guagliardi, A.; Moliterni, A.; Polidori, G.; Spagna, R. SIR97; 1999.
93. DIRDIF99: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-99 program system; Technical Report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1999.
94. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. 4.
95. CrystalStructure 3.8.0; Crystal Structure Analysis Package; Rigaku and Rigaku/MSC: The Woodlands, TX, 2000-2006.
96. Carruthers, J. R.; Rollett, J. S.; Betteridge, P. W.; Kinna, D.; Pearce, L.; Larsen, A.; Gabe, E. CRYSTALS Issue 11; Chemical Crystallography Laboratory: Oxford, U.K., 1999.