Chiral hydride and dihydrogen pincer-type complexes of osmium

Organometallics

Volumn 26, Issue 23, 2007, Pages 5661-5666

  Kuznetsov, Vladimir F ^a,b   Gusev, Dmitry G ^a  

^a WILFRID LAURIER UNIVERSITY   (Canada)

^b Cody Laboratories ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE COMPLEXES; CHIRAL HYDRIDES; DFT COMPUTATIONAL TECHNIQUES; DIHYDROGEN PINCERS;

CHIRALITY; DENSITY FUNCTIONAL THEORY; LIGANDS; REACTION KINETICS; SPECTROSCOPIC ANALYSIS;

OSMIUM COMPOUNDS;

EID: 36249004004     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700651g     Document Type: Article

References (48)

1. For reviews see: (a) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
2. (b) Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055.
3. (c) Bedford, R. B. Chem. Commun. 2003, 1787.
4. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837.
5. (e) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
6. (f) Milstein, D. Pure Appl. Chem. 2003, 75, 2003.
7. (g) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
8. (h) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917.
9. (i) Vigalok, A.; Milstein, D. Acc Chem. Res. 2001, 34, 798.
10. (j) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3006.
11. (k) Jensen, C. M. Chem. Commun. 1999, 2443.
12. (a) Aydin, J.; Kumar, K. S.; Sayah, M. J.; Wallner, O. A.; Szabó, K. J. J. Org. Chem. 2007, 72, 4689.
13. (b) Rubio, M.; Suárez, A.; del Rio, D.; Galindo, A.; Alvarez, E.; Pizzano, A. Dalton Trans. 2007, 4, 407.
14. (c) Yoon, M. S.; Ramesh, R.; Kim, J.; Ryu, D.; Ahn, K. H. J. Organomet. Chem. 2006, 697, 5927.
15. (d) Baber, R. A.; Bedford, R. B.; Betham, M.; Blake, M. E.; Coles, S. J.; Haddow, M. F.; Hursthouse, M. B.; Orpen, A. G.; Pilarski, L. T.; Pringle, P. G.; Wingad, R. L. Chem. Commun. 2006, 3880.
16. (e) Gosiewska, S.; Huis in't Veld, M.; De Pater, J. J. M.; Bruijnincx, P. C. A.; Lutz, M.; Spek, A. L.; Van Koten, G.; Klein Gebbink, R. J. M. Tetrahedron: Asymmetry 2006, 17, 674.
17. (f) Benito-Garagorri, D.; Bocokiæ V.; Mereiter, K.; Kirchner, K. Organometallics 2006, 25, 3817.
18. (g) Wallner, O. A.; Olsson, V. J.; Eriksson, L.; Szabó, K. J. Inorg. Chim. Acta 2006, 359, 1767.
19. (h) Hao, X.-Q.; Gong, J.-F.; Du, C-X.; Wu, L.-Y.; Wu, Y.-J.; Song, M.-P Tetrahedron Lett. 2006, 47, 5033.
20. (i) Soro, B.; Stoccoro, S.; Minghetti, G.; Zueca, A.; Cinellu, M. A.; Manassero, M.; Gladiali, S. Inorg. Chim. Acta. 2006, 359, 1879.
21. (j) Motoyama, Y.; Shimozono, K.; Nishiyama, H. Inorg. Chim. Acta 2006, 359, 1725.
22. (k) Benito-Garagorri, D.; Becker, E.; Wiedermann, J.; Lackner, W.; Pollak, M.; Mereiter, K.; Kisala, J.; Kirchner, K. Organometallics 2006, 25, 1900.
23. (l) Medici, S.; Gagliardo, M.; Williams, S. B.; Chase, P. A.; Gladiali, S.; Lutz, M.; Spek, A. L.; van Klink, G. P. M.; van Koten, G. HeIv. Chim. Acta 2005, 88, 694.
24. (m) Morales-Morales, D.; Cramer, R. E.; Jensen, C. M. J. Organomet. Chem. 2002, 654, 44.
25. (n) Williams, B. S.; Dani, P.; Lutz, M.; Spek, A. L.; van Koten, G. Helv. Chim. Acta 2001, 84, 3519.
26. (o) Dani, P.; Albrecht, M.; van Klink, G. P. M.; van Koten, G. Organometallics 2000, 19, 4468.
27. (p) Longmire, J. M.; Zhang, X.; Shang, M. Organometallics 1998, 17, 4374.
28. (q) Karlen, T.; Dani, P.; Grove, D. M.; Steenwinkel, P.; van Koten, G. Organometallics 1996, 15, 5687.
29. (r) Gorla, F.; Togni, A.; Venanzi, L. M.; Albinati, A.; Lianza, F. Organometallics 1994, 13, 1607.
30. (a) Kuznetsov, V. F.; Lough, A. J.; Gusev, D. G. Chem. Commun. 2002, 2432.
31. (b) Kuznetsov, V. F.; Lough, A. J.; Gusev, D. G. Inorg. Chim. Acta 2006, 359, 2806.
32. t] is abbreviated as PGP.
33. 2) despite the fact that the standard deviations are all within 0.002 A.
34. (a) Desrosiers, P. J.; Cai, L.; Lin, Z.; Richards, R.; Halpern, J. J. Am. Chem. Soc. 1991, 113, 4173.
35. 1)]/0.937.
36. (a) Gusev, D. G. J. Am. Chem. Soc. 2004, 126, 14249.
37. (b) Calculated using eq 3 from ref 7a.
38. (a) Smith, K.-T.; Tilset, M.; Kuhlman, R.; Caulton, K. G. J. Am. Chem. Soc. 1995, 117, 9473.
39. (b) Gusev, D. G.; Dolgushin, F. M.; Antipin, M. Yu. Organometallics 2001, 20, 1001.
40. (c) Grellier, M.; Vendier, L; Chaudret, B.; Albinati, A.; Rizzato, S. Mason, S.; Sabo-Etienne, S. J. Am. Chem. Soc. 2005, 127, 17592, and references therein.
41. Gusev, D. G.; Dolgushin, F. M.; Antipin, M. Yu. Organometallics 2001, 20, 1001.
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.05; Gaussian, Inc.: Wallingford, CT, 2004.
43. (a) Adamo, C.; Barone V. J. Chem. Phys. 1998, 108, 664.
44. (b) Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533.
45. (c) Burke K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F., Vignale, G., Das, M. P., Eds.; Plenum: New York, 1998.
46. (a) Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
47. (b) Zhao, Y.; Pu, J.; Lynch, B. J.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2004, 6, 673.
48. For more information about basis sets implemented in Gaussian 03 and references see: Frish, A.; Frish, M. J.; Trucks, G. W. Gaussian 03 User's Reference; Gaussian, Inc.: Pittsburgh, PA, 2003. The basis sets are also available from the Extensible Computational Chemistry Environment Basis Set Database, which is developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory, which is part of the Pacific Northwest Laboratory, P.O. Box 999, Richland, WA 99352 (www.emsl.pnl.gov/forms/basisform.html).