Pincer CNN ruthenium(II) complexes with oxygen-containing ligands (O 2CR, OAr, OR, OSiR3,O3SCF3): Synthesis, structure, and catalytic activity in fast transfer hydrogenation

Organometallics

Volumn 28, Issue 15, 2009, Pages 4421-4430

  Baratta, Walter ^a   Ballico, Maurizio ^a   Zotto, Alessandro Del ^a   Herdtweck, Eberhardt ^b   Peloso, Santo Magnolia Riccardo ^a   Siega, Katia ^a   Toniutti, Micaela ^a   Zangrando, Ennio ^c   Rigo, Pierluigi ^a  

^a UNIVERSITY OF UDINE   (Italy)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2-PROPANOL; ACTIVE CATALYST; ALKOXIDE COMPLEXES; ALKOXIDES; CATALYTIC ACTIVITY; FAST TRANSFER; HIGH YIELD; HYDROGEN BOND INTERACTION; INTRAMOLECULAR INTERACTIONS; LIGAND EXCHANGES; MONODENTATES; OXYGEN DONOR LIGANDS; OXYGEN-CONTAINING LIGANDS; PINCER COMPLEXES; RUTHENIUM COMPLEXES; SILANOLATES; TRIFLATES; X-RAY STUDIES;

BINDING SITES; CARBOXYLATION; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; HYDROGEN; HYDROGEN BONDS; KETONES; LIGANDS; OXYGEN; PHENOLS; RUTHENIUM; RUTHENIUM COMPOUNDS; SODIUM; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL); THALLIUM; THALLIUM COMPOUNDS;

COMPLEXATION;

EID: 68149183467     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900274r     Document Type: Article

References (109)

1. (a) The Handbook of Homogeneous Hydrogénation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; Vols. 1-3.
2. (b) Asymmetric Catalysis on Industrial Scale; Blaser, H.-U., Schmidt, E., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
3. (c) Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 29.
4. (d) Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
5. (e) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetrie Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 1.
6. (a)Baratta, W.; Rigo, P. Ew. J. Inorg. Chem. 2008, 4041.
7. (b) Wang, C.; Wu, X.; Xiao, J. Chem. Asian J. 2008, 3, 1750.
8. (c) Morris, D. J.; Wills, M. Chim. Oggi 2007, 25, 11.
9. (d) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300.
10. (e) Samec, J. S. M.; Bäckvall, J. E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006, 35, 237.
11. (f ) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.
12. (g) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
13. (h) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201.
14. (a)Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
15. (b) Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
16. (a) Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.
17. (b) Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
18. (c) Petra, D. G. I.; Reek, J. N. H.; Handgraaf, J. W.; Meijer, E. J.; Dierkes, P.; Kamer, P. C. J.; Brussee, J.; Schoemaker, H. E.; van Leeuwen, P W N. M. Chem. Eur. J. 2000, 6, 2818.
19. Handgraaf, J. W.; Meijer, E. J. J. Am. Chem. Soc. 2007, 129, 3099.
20. Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2008, 130, 11979.
21. (a) Baratta, W.; Chelucci, G.; Herdtweck, E.; Magnolia, S.; Siega, K.; Rigo, P. Angew. Chem., Int. Ed 2007, 46, 7651.
22. (b) Baratta, W.; Herdtweck, E.; Siega, K.; Toniutti, M.; Rigo, P. Organometallics 2005, 24, 1660.
23. (a) Reetz, M. T.; Li, X. J. Am. Chem. Soc. 2006, 128, 1044.
24. (b) Hayes, A. M.; Morris, D. J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2005, 127, 7318.
25. (c) Cuervo, D.; Gamasa, M. P.; Gimeno, J. Chem. Eur. J. 2004, 10, 425.
26. (d) Rautenstrauch, V.; Hoang-Cong, X.; Churlaud, R.; Abdur-Rashid, K.; Morris, R. H. Chem. Eur. J. 2003, 9, 4954.
27. (e) Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2291.
28. (f) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 52, 6104.
29. (a) Baratta, W.; Chelucci, G.; Gladiali, S.; Siega, K.; Toniutti, M.; Zanette, M.; Zangrando, E.; Rigo, P. Angew. Chem., Int. Ed. 2005, 44, 6214.
30. (b) Baratta, W.; Bosco, M.; Chelucci, G.; Del Zotto, A.; Siega, K.; Toniutti, M.; Zangrando, E.; Rigo, P. Organometallics 2006, 25, 4611.
31. (c) Baratta, W.; Siega, K.; Rigo, P. Adv. Synth. Catal. 2007, 349, 1633.
32. (d) Baratta, W.; Ballico, M.; Baldino, S.; Chelucci, G.; Herdtweck, E.; Siega, K.; Magnolia, S.; Rigo, P. Chem. Eur. J. 2008, 14, 9148.
33. Turnover frequency (moles of ketone or aldehyde converted into alcohol per mole of catalyst per hour) at 50% conversion.
34. (a) Zeng, F.; Yu, Z. Organometallics 2008, 27, 2898.
35. (b) Mothes, E.; Sentets, S.; Luquin, M. A.; Mathieu, R.; Lugan, N.; Lavigne, G. Organometallics 2008, 27, 1193.
36. (c) Zweifel, T.; Naubron, J. V.; Büttner, T.; Ott, T.; Grützmacher, H. Angew. Chem., Int. Ed. 2008, 47, 3245.
37. (d) Lundgren, R. J.; Rankin, M. A.; McDonald, R.; Schatte, G.; Stradiotto, M. Angew. Chem., Int. Ed. 2007, 46, 4732.
38. (e) Gagliardo, M.; Chase, P. A.; Brouwer, S.; van Klink, G. P. M.; van Koten, G. Organometallics 2007, 26, 2219.
39. (f) Clarke, Z. E.; Maragh, P. T.; Dasgupta, T. P.; Gusev, D. G.; Lough, A. J.; Abdur-Rashid, K. Organometallics 2006, 25, 4113.
40. (g) Braunstein, P.; Fryzuk, M. D.; Naud, F.; Rettig, S. J. J. Chem. Soc, Dalton Trans. 1999, 589.
41. (h) Yang, H.; Alvarez-Gressier, M.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 1401.
42. Baratta, W.; Chelucci, G.; Magnolia, S.; Siega, K.; Rigo, P. Chem. Eur. J. 2009, 15, 126.
43. (a) Baratta, W.; Ballico, M.; Del Zotto, A.; Siega, K.; Magnolia, S.; Rigo, P. Chem. Eur. J. 2008, 14, 2557.
44. (b) Baratta, W; Ballico, M.; Chelucci, G.; Siega, K.; Rigo, P Angew. Chem., Int. Ed. 2008, 47, 4362.
45. (a) Jacobsen, H.; Berke, H. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: Amsterdam, 2001; Chapter 4, p 89.
46. (b) Pamies, O.; Bäckvall, J. E. Chem. Eur. J. 2001, 7, 5052.
47. (c) Aranyos, A.; Csjemyik, G.; Szabó, K. J.; Bäckvall, J. E. Chem. Commun. 1999, 351.
48. (a) Baratta, W.; Ballico, M.; Esposito, G.; Rigo, P. Chem. Eur. J. 2008, 14, 5588.
49. (b) Baratta, W; Siega, K.; Rigo, P. Chem. Eur. J. 2007, 13, 7479.
50. (a) Hoffman, D. M.; Lappas, D.; Wierda, D. A. J. Am. Chem. Soc. 1989, 111, 1531.
51. (b) Esteruelas, M. A.; Valero, C.; Oro, L. A.; Meyer, U.; Werner, H. Inorg. Chem. 1991, 30, 1159.
52. (a) Fulton, J. R.; Holland, A. W.; Fox, D. J.; Bergman, R. G. Acc Chem. Res. 2002, 35, 44.
53. (b) Bradley, D. C.; Mehrotra, R. C.; Rothwell, I. P.; Singh, A. In Alkoxo and Aryloxo Derivatives of Metals; Academic Press: New York, 2001.
54. (c) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
55. (a) Yin, X.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27.
56. (b) Gibson, D. H. Coord. Chem. Rev. 1999, 185-186, 335.
57. (c) Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 344.
58. (d) Jessop,P. G.; Ikariya, T; Noyori, R. Chem. Rev. 1995, 95, 259.
59. (e) Aresta, M.; Quaranta, E.; Tommasi, I. New J. Chem. 1994, 18, 133.
60. (f) Whittlesey, M. K.; Perutz, R. N.; Moore, M. H. Organometallics 1996, 15, 5166.
61. (g) Burling, S.; Kociok-Köhn, G.; Mahon, M. F.; Whittlesey, M. K.; Williams, J. M. J. Organometallics 2005, 24, 5868.
62. (a) Espinet, P.; Albéniz, A. C. In Fundamentals of Molecular Catalysis; Kurosawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Current Methods in Inorganic Chemistry Vol. 3, Chapter 6, p 332.
63. (b) Eisenberg, R.; Hendriksen, D. E. Adv. Catal. 1979, 28, 79.
64. Koike, T.; Ikariya, T. Adv. Synth. Catal. 2004, 346, 37.
65. (a) Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104.
66. (b) Abdur-Rashid, K.; Abbel, R.; Hadzovic, A.; Lough, A. J.; Morris, R. H. Inorg. Chem. 2005, 44, 2483.
67. (a) Field, L. D.; Lawrenz, E. T.; Shaw, W. J.; Turner, P. Inorg. Chem. 2000, 39, 5632.
68. (b) Albéniz, M. J.; Esteruelas, M. A.; Lledós, A.; Maseras, F.; Oñate, E.; Oro, L. A.; Sola, E.; Zeier, B. J. Chem. Soe, Dalton Trans. 1997, 181.
69. Brandenburg, K.; Diamond, Version 3.1d; Crystal Impact GbR, Bonn, Germany, 2006.
70. (a) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
71. (b) Brammer, L. Dalton Trans. 2003, 3145.
72. (c) Aullön, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653.
73. (a) Kuznetsov, V. F.; Yap, G. P. A.; Alper, H. Organometallics 2001, 20, 1300.
74. (b) Wong, W.-K.; Lai, K.-K.; Tse, M.-S.; Tse, M.-C.; Gao, J.-X.; Wong, W-T.; Chan, S. Polyhedron 1994, 13, 2751.
75. (a) Clapham, S. E.; Guo, R.; Zimmer-De Iuliis, M.; Rasool, N.; Lough, A. J.; Morris, R. H. Organometallics 2006, 25, 5477.
76. (b) Koike, T.; Ikariya, T. Organometallics 2005, 24, 724.
77. (c) Kapteijn, G. M.; Dervisi, A.; Grove, D. M.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 10939.
78. (d) Osakada, K.; Ohshiro, K.; Yamamoto, A. Organometallics 1991, 10, 404.
79. (e) Kim, Y J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096.
80. (f) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563.
81. Šefčík, J.; Rankin, S. E.; Kirchner, S. J.; McCormick, A. V. J. Non-Cryst. Solids 1999, 258, 187.
82. Damrauer, R.; Simon, R.; Krempp, M. J. Am. Chem. Soc. 1991, 113, 4431.
83. Haiduc, I. Organometallics 2004, 23, 3.
84. (a) Marciniec, B.; Maciejewski, H. Coord. Chem. Rev. 2001, 223, 301.
85. (b) Johnson, T. J.; Folting, K.; Streib, W E.; Martin, J. D.; Huffman, J. C.; Jackson, S. A.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1995, 34, 488.
86. (c) Poulton, J. T.; Folting, K.; Streib, W. E.; Caulton, K. G. Inorg. Chem. 1992, 57, 3190.
87. (a) Lawrance, G. A. Chem. Rev. 1986, 86, 17.
88. (b)Beck, W.; Siinkel, K. Chem. Rev. 1988, 88, 1405.
89. (a) Geldbach, T. J.; Rüegger, H.; Pregosin, P. S. Magn. Reson. Chem. 2003, 41, 703.
90. (b) Belli Dell'Amico, D.; Calderazzo, F.; Grazzini, A.; Labella, L.; Marchetti, F. Inorg. Chim. Acta 2002, 334, 411.
91. (c) Bickley, J. F.; Higgins, S. J.; Stuart, C. A.; Steiner, A. Inorg. Chem. Commun. 2000, 3, 211.
92. (d) Feher, F. J.; Baldwin, R. K.; Ziller, J. W. Acta Crystallogr. 2000, C56, 633.
93. (e) Mahon, M. F.; Whittlesey, M. K.; Wood, P T. Organometallics 1999, 18, 4068.
94. (f) Blosser, P. W; Gallucci, J. C.; Wojcicki, A. Inorg. Chem. 1992, 31, 2376.
95. (a) Pavlik, S.; Mereiter, K.; Puchberger, M.; Kirchner, K. Organometallics 2005, 24, 3561.
96. (b) Fossey, J. S.; Matsubara, R.; Vital, P.; Kobayashi, S. Org. Biomol. Chem. 2005, 3, 2910.
97. (c) Arnold, D. L.; Cotton, F. A.; Matonic, J. H.; Murillo, C. A. Polyhedron 1997, 16, 1837.
98. (d) Feazell, R. P.; Carson, C. E.; Klausmeyer, K. K. Eur. J. Inorg. Chem. 2005, 3287.
99. Jones, V. A.; Sriprang, S.; Thornton-Pett, M.; Kee, T. P. J. Organomet. Chem. 1998, 567, 199.
100. (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
101. (b) Coliman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Application of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
102. Meyerstein, D. Coord. Chem. Rev. 1999, 185-186, 141.
103. Buzzeo, M. C.; Zakharov, L. N.; Rheingold, A. L.; Doerrer, L. H. J. Mol. Struct. 2003, 657, 19.
104. CrysAlis Data Collection Software and Data Processing Software for Oxford Xcalibur diffractometer, Version 1.171; Oxford Diffraction Ltd., Oxfordshire, U.K., 2005.
105. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Macromolecular Crystallography, Part A; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; Methods in Enzymology Vol. 276, pp 307-326.
106. (a) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. SIR92. J. Appl. Crystallogr. 1994, 27, 435.
107. (b) Sheldrick, G. M. SHELXL-97; University of Göttingen, Göttingen, Germany, 1998.
108. (c) Spek, A. L.; PLATON; Utrecht University, Utrecht, The Netherlands, 2008.
109. (d) Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.