Mechanistic studies on the copper-catalyzed hydrosilylation of ketones

European Journal of Inorganic Chemistry

Volumn , Issue 4, 2010, Pages 529-541

  Issenhuth, Jean Thomas ^a   Notter, François Paul ^a   Dagorne, Samuel ^a   Dedieu, Alain ^a   Bellemin Laponnaz, Stéphane ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

Author keywords

Asymmetric catalysis; Copper; Density functional calculations; Hydrosilylation; Mechanistic studies

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; DENSITY FUNCTIONAL THEORY; HYDROSILYLATION; ISOTOPES; REACTION INTERMEDIATES;

ASYMMETRIC CATALYSIS; CATALYZED REACTIONS; COMPUTATIONAL STUDIES; COPPER CATALYZED; DENSITY-FUNCTIONAL CALCULATIONS; DFT-B3LYP; ENANTIOPURE; HYDROSILYLATIONS; MECHANISTIC STUDIES; SECONDARY ALCOHOLS;

KETONES;

EID: 75749092923     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200900961     Document Type: Article

References (91)

1. E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer-Verlag, New York, 1999.
2. H. Nishiyama, K. Itoh, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, ch. 2.
3. a) I. Ojima, M. Nihonyanagi, Y. Nagai, J. Chem. Soc. Chem. Commun. 1972, 938;
4. b) R. J. P. Corriu, U.E. Moreau, J. Chem. Soc. Chem. Commun. 1973, 38;
5. c) W. Dumont, J. C. Poulin, T.P. Dang, H. B. Kagan, J. Am. Chem. Soc. 1973, 95, 8295.
6. Selected examples: a) H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, K. Itoh, Organometallics 1989, 8, 846;
7. b) M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. Int. Ed. Engl. 1994, 33, 111;
8. c) A. Sudo, H. Yoshida, K. Saigo, Tetrahedron: Asymmetry 1997, 8, 3205;
9. d) B. Tao, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 3892;
10. e) D. A. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534;
11. f) V. César, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2005, 11, 2862.
12. For mechanistic investigations of rhodium-catalyzed hydrosilylation of ketones, see: a) I. Ojima, T. Kogure, M. Kumagai, S. Horiuchi, Y. Sato, J. Organomet. Chem, 1976, 122, 83;
13. b) G. Z. Zheng, T. H. Chan, Organometallics 1995, 14, 70;
14. c) C Reyes, A. Prock, W. P. Giering, Organometallics 2002, 21, 546;
15. d) N. Schneider, M. Finger, C Haferkemper, S. Bellemin-Laponnaz, P. Hofmanu, L. H. Gade, Angew. Chem. Int. Ed. 2009, 48, 1609;
16. e) N. Schneider, M. Finger, C. Haferkemper, S. Bellemin-Laponnaz, P. Hofmann, L. H. Gade, Chem. Eur. J. 2009, 15, 11515.
17. a) G. Zhu, M. Terry, X. Zhang, J. Organomet. Chem. 1997, 547, 97;
18. b) Y. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1998, 17, 3420;
19. c) C Moreau, C. G. Frost, B. Murrer, Tetrahedron Lett. 1999, 40, 5617.
20. a) H. Mimoun, J. Y. de Saint Laumer, L. Giannini, R. Scopelliti, C. Floriani, J. Am, Chem. Soc. 1999, 121, 6158;
21. b) V. Bette, A. Mortreux, D. Savoia, J.F. Carpentier, Tetrahedron 2004, 60, 2837;
22. c) V Bette, A. Mortreux, D. Savoia, J.-F. Carpentier, Adv. Synth. Catal. 2005, 347, 289.
23. J. Yun, S. L. Buchwald, J. Am. Chem, Soc. 1999, 121, 5640.
24. a) B. K. Langlotz, H. Wadepohl, L. H. Gade, Angew. Chem. Int. Ed. 2008, 47, 4670;
25. b) N. S. Shaikh, S. Enthaler, K. Junge, M, Beller, Angew. Chem. Int. Ed. 2008, 47, 2497.
26. For reviews on hydrosilylation of ketones, see: a) J.F. Carpentier, V. Bette, Curr. Org. Chem. 2002, 6, 913;
27. b) O. Riant, N. Mostefa'i, J. Courmacel, Synthesis 2004, 2943;
28. c) C. Deutsch, N. Krause, B. H. Lipshutz, Chem. Rev. 2008, 108, 2916;
29. d) S. Diez-González, S. P. Nolan, Acc. Chem. Res. 2008, 41, 349.
30. H. Brunner, W. Miehling, J. Organomet. Chem. 1984, 275, C171.
31. B. H. Lipshutz, K. Noson, W. Chrisman, J. Am. Chem. Soc. 2001, 123, 12917.
32. For other examples of copper-based systems for asymmetric hydrosilylation of ketones, see: a) S. Sirol, J. Courmacel, N. Mostefaï, O. Riant, Org. Lett. 2001, 3, 4111;
33. b) J. Courmacel, N. Mostefaï, S. Sirol, S. Chopin, O. Riant, Isr. J. Chem, 2002, 41, 231;
34. c) D.w. Lee, J. Yun, Tetrahedron Lett. 2004, 45, 5415;
35. d) J. Wu, J.X. Ji, A. S. C. Chan, Proc. Natl. Acad, Sci. USA 2005, 102, 3570;
36. e) M., L. Kantam, S. Laha, J. Yadav, P. R. Likhar, B. Sreedhar, B. M. Choudary, Adv. Synth. Catal. 2007, 349, 1797;
37. f) N. Mostefaï, S. Sirol, J. Courmacel, O. Riant, Synthesis 2007, 8, 1265;
38. g) M. L. Kantam, S. Laha, J. Yadav, P. R. Likhar, B. Sreedhar, S. Jha, S. Bhargava, M. Udayakiran, B. Jagadeesh, Org. Lett. 2008, 10, 2979.
39. a) D. H. Appella, Y. Moritani, R. Shintani, E. M. Ferreira, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473;
40. b) Y. Moritani, D. H. Appela, V. Jurkauskas, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 6797.
41. B. H. Lipshutz, K. Noson, W. Chrisman, A. Lower, J. Am. Chem. Soc 2003, 125, 8779.
42. J. T. Issenhuth, S. Dagorne, S. Bellemin-Laponnaz, Adv. Synth. Catal. 2006, 348, 1991.
43. H. Ito, T. Ishizuka, T. Okumura, H. Yamanaka, J. Tateiwa, M. Sonoda, A. Hosomi, J. Organomet. Chem, 1999, 574, 102.
44. Two different diphosphane ligands were used in this study: 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl (BINAP) and 2,2-dimethyl-1,3- bis(diphenylphosphanyl)propane (DMDP).
45. F. P. Notter, Ph. D. Thesis, Université de Strasbourg, 2008.
46. a) H. Tamura, H. Yamasaki, H. Sato, S. Sakaki, J. Am. Chem. Soc. 2003, 125, 16114;
47. b) S. Sakaki, T. Takayama, M. Sumimoto, M. Sugimoto, J. Am. Chem. Soc. 2004, 126, 3332;
48. c) M. Sumimoto, N. Iwane, T. Takahama, S. Sakaki, J. Am. Chem. Soc. 2004, 126, 10457;
49. d) B. O. Leung, D. L. Reid, D. A. Armstrong, A. Rauk, J. Phys. Chem. A 2004, 108, 2720;
50. e) A. A. C. Braga, G. Ujaque, F. Maseras, Organometallics 2006, 25, 3647;
51. f) P. Deglmann, E. Ember, P. Hofmanu, S. Pitter, O. Walter, Chem. Ew. J. 2007, 13, 2864.
52. S. C. A. H. Pierrefixe, F. M. Bickelhaupt, Struct. Chem. 2007, 18, 813.
53. R. Hoffmann, J. M. Howell, E. L. Muetterties, J. Am. Chem. Soc, 1972, 94, 3047.
54. S. C. A. Y. Pierrefixe, C. F. Guerra, F. M. Bickelhaupt, Chem. Eur. J. 2008, 14, 819.
55. M. Onda, Y. Kohama, K. Suga, I. Yamaguchi, J. Mol. Struct. 1998, 442, 19.
56. G. De Luca, M. Longen, G. Pileio, P. Lantto, ChemPhysChem 2005, 6, 2086.
57. a) T. Miyahara, T. Inazu, THEOCHEM 1996, 364, 131;
58. b) A. N. Rodriguez, F. A. Giannini, H. A. Baldoni, L. N. Santagata, M. A. Zamora, S. Zacchino, C. P. Sosa, R. D. Enriz, I. G. Csizmadia, THEOCHEM 1999, 463, 271.
59. P Milko, J. Roithova, D. Schroder, J. Lemaire, H. Schwarz, M. C. Holthausen, Chem, Eur. J. 2008, 14, 4318.
60. T.H. Chan, A. Melnyk, J. Am. Chem. Soc. 1970, 92, 3718.
61. J.X. Chen, J. F. Daeuble, D. M. Brestensky, J. M. Stryker, Tetrahedron 2000, 56, 2153.
62. a) M. R. Churchill, S. A. Bezman, J. A. Osborn, J. Wormald, Inorg. Chem, 1972, 11, 1818;
63. b) T. H. Lemmen, K. Folting, J. C. Huffman, K. G. Caulton, J. Am. Chem, Soc. 1985, 107, 7774.
64. G. V. Goeden, J. C Huffman, K. G. Caulton, Inorg. Chem. 1986, 25, 2484.
65. N. P. Mankad, D. S. Laitar, J. P. Sadighi, Organometallics 2004, 23, 3369-3371.
66. 32] and for example: a) L. A. Goj, E. D. Blue, C. Munro-Leighton, T. B. Gunnoe, J. L. Petersen, Inorg. Chem. 2005, 44, 8647-8649;
67. b) L. A. Goj, E. D. Blue, S. A. Delp, T. B. Gunnoe, T. R. Cundari, A. W. Pierpont, J. L. Petersen, P. D. Boyle, Inorg. Chem. 2006, 45, 9032-9045;
68. c) K. X. Bhattacharyya, J. A. Akana, D. S. Laitar, J. M. Berlin, J. P. Sadighi, Organometallics 2008, 27, 2682-2684;
69. NHC ligands have allowed complete characterization of monomeric gold(I) hydride complexes, see: d) E. Y. Tsui, P. Müller, J. P. Sadighi, Angew. Chem, Int. Ed. 2008, 47, 8937-8940.
70. G. V. Goeden, K. G. Caulton, J. Am. Chem. Soc. 1981, 103, 7354.
71. 6 is probably at a lower aggregate (possibly monomeric), see: a) W. S. Mahoney, J. M. Stryker, J. Am. Chem. Soc. 1989, 111, 8818;
72. b) J.X. Chen, J. F. Daeuble, D. M. Brestensky, J. M. Stryker, Tetrahedron 2000, 56, 2153.
73. T. Satyanarayana, S. Abraham, H. B. Kagan, Angew. Chem. Int. Ed. 2009, 48, 456.
74. 2 as silane: see data in Supporting Information
75. M. Kitamura, S. Suga, H. Oka, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800.
76. -1, see: M. Steigelmann, Y. Nisar, F. Rominger, B. Goldfuss, Chem. Eur. J. 2002, 8, 5211.
77. We are well aware however that the DFT calculations may not take properly into account weak interactions such as π-π interactions or CH/π interactions. Thus the agreement between theory and experiment may be regarded as fortuitous. Yet the overall consistency of the experimental and theoretical results adds credence to our final conclusions.
78. 2 and found that decomposition by thermolysis (at 200°C for 20 min) of the complex could lead to a mixture of benzophenone and diphenylmethanol, see: K. Osakada, T. Takizawa, M. Tanaka, T. Yamamoto, J. Organomet. Chem. 1994, 473, 359.
79. A catalytic cycle that contains an enantioselectivity determining step different from the rate limiting step was also postulated for the titanium-catalyzed hydrosilylation of ketones. The hypothesis was proposed based on the rate enhancement when alcohol was added to the reaction mixture. Such a positive alcohol effect was also observed in some cases with copper hydride-catalyzed reactions, see references 8 and 10c.
80. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098;
81. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785;
82. c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
83. 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, V. Bakken, 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, J. A. Pople, Gaussian 03, Revision B.04 ed., Gaussian, Inc., Pittsburgh, PA, 2003.
84. a) P. C. Hariharan, J. A. Pople, Mol. Phys. 1974, 27, 209;
85. b) P. C. Hariharan, J. A. Pople, Chem. Phys. Lett. 1972, 16, 217.
86. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297.
87. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571.
88. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem.Phys. 1980, 72, 650.
89. D. Andrae, U. Haüssermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123.
90. A. Schäfer, R. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829.
91. S. Rendler, O. Plefka, B. Karatas, G. Auer, R. Fröhlich, C. Mück-Lichtenfeld, S. Grimme, M. Oestreich, Chem. Eur. J. 2008, 14, 11512-11528.