On the mechanism of iridium-catalyzed asymmetric hydrogenation of imines and alkenes: A theoretical study

Organometallics

Volumn 30, Issue 9, 2011, Pages 2483-2497

  Hopmann, Kathrin Helen ^a   Bayer, Annette ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE HYDROGENATION; ALKENE SUBSTRATE; ASYMMETRIC HYDROGENATION; CATALYTIC CYCLES; DIFFERENT MECHANISMS; ENANTIOSELECTIVE HYDROGENATION; HYDROGENATION REACTIONS; IRIDIUM COMPLEX; MECHANISTIC ASPECTS; OXAZOLINES; QUANTUM-MECHANICAL STUDY; REACTION CONDITIONS; REACTION CYCLES; REACTION MECHANISM; THEORETICAL STUDY; UNFUNCTIONALIZED ALKENES;

COORDINATION REACTIONS; ENANTIOSELECTIVITY; IRIDIUM; IRIDIUM COMPOUNDS; NITROGEN COMPOUNDS; OLEFINS; PHOSPHORUS COMPOUNDS; QUANTUM THEORY; STEREOCHEMISTRY; SUBSTRATES;

HYDROGENATION;

EID: 79955591931     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1009507     Document Type: Article

References (44)

1. Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272
2. Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, No. 1 + 2, 33.
3. Crabtree, R. Acc. Chem. Res. 1979, 12, 331
4. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336
5. Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402
6. Schnider, P.; Koch, G.; Prétot, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. - Eur. J. 1997, 3, 887
7. Baeza, A.; Pfaltz, A. Chem. - Eur. J. 2010, 16, 4003
8. Dietiker, R.; Chen, P. Angew. Chem., Int. Ed. 2004, 43, 5513
9. Brandt, P.; Hedberg, C.; Andersson, P. G. Chem. - Eur. J. 2003, 9, 339
10. Fan, Y.; Cui, X.; Burgess, K.; Hall, M. B. J. Am. Chem. Soc. 2004, 126, 16688
11. Church, T. L.; Rasmussen, T.; Andersson, P. G. Organometallics 2010, 29, 6769
12. Balcells, D.; Noca, A.; Clot, E.; Gnanamgari, D.; Crabtree, R. H.; Eisenstein, O. Organometallics 2008, 27, 2529
13. Herrera, V.; Muñoz, B.; Landaeta, V.; Canduas, N. J. Mol. Catal. A: Chem. 2001, 174, 141
14. Landaeta, V. R.; Muñoz, B.; Peruzzini, M.; Herrera, V.; Bianchini, C.; Sánchez-Delgado, R. A. Organometallics 2006, 25, 403
15. Landaeta, V. R.; Peruzzini, M.; Herrera, V.; Bianchini, C.; Sánchez-Delgado, R. A.; Goeta, A. E.; Zanobini, F. J. Organomet. Chem. 2006, 691, 1039
16. Fabrello, A.; Bacheliera, A.; Urrutigoïtya, M.; Kalcka, P. Coord. Chem. Rev. 2010, 254, 273-287
17. Martín, M.; Sola, E.; Tejero, S.; Andrés, J.-L.; Oro, L. A. Chem. - Eur. J. 2006, 12, 4043
18. Martín, M.; Sola, E.; Tejero, S.; Lopéz, J. A.; Oro, L. A. Chem. - Eur. J. 2006, 12, 4057
19. Becke, A. D. Phys. Rev. A 1988, 38, 3098
20. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; 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, I.; 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 E.01; Gaussian, Inc.: Wallingford, CT, 2004.
22. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H.F., III, Ed.; Plenum: New York, 1976; Vol. 3, p 1.
23. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
24. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 284
25. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
26. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
27. Tomasi, J.; Mennucci, B.; Cancès, E. J. Mol. Struct. (THEOCHEM) 1999, 464, 211
28. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
29. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024
30. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
31. GAMESS, Version: 1 Oct 2010 (R1): Schmidt, M. W.; Baldrige, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; NGyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A., Jr. J. Comput. Chem. 1993, 14, 1347.
32. Reiher, M.; Salomon, O.; Hess, B. A. Theor. Chem. Acc. 2001, 107, 48-55
33. Mazet, C.; Smidt, S. P.; Meuwly, M.; Pfaltz, A. J. Am. Chem. Soc. 2004, 126, 14176
34. The notation "above" and "below" the plane refers to the complex orientation as shown in Figure 3, i.e., with the isopropyl substituent above the plane.
35. The energies are given relative to the substrate-coordinated dihydride species.
36. Enthalpies were computed at B3LYP/LANL2DZ geometries with 6-311+G(d,p) on all atoms except Ir, for which SDD augmented by a polarization function (0.65) was employed. (9)
37. Cui, X.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14212
38. Perry, M. C.; Cui, X.; Powell, M. T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 113
39. Cozzi, P. G.; Menges, F.; Kaiser, S. Synlett 2003, 6, 833
40. Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897
41. Heinekey, D. M.; Lledós, A.; Lluch, J. M. Chem. Soc. Rev. 2004, 33, 175
42. B, Supporting Information Figure S 2 (1.66 Å for H-H and 1.56 and 1.57 Å for Ir-H).
43. Zhu, Y.; Fan, Y.; Burgess, K. J. Am. Chem. Soc. 2010, 132, 6249
44. Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Zhu, G. J. Am. Chem. Soc. 2005, 127, 7805