Oxidative addition of RCO2H and HX to chiral diphosphine complexes of iridium(I): Convenient synthesis of mononuclear halo-carboxylate iridium(III) complexes and cationic dinuclear triply halogen-bridged iridium(III) complexes and their catalytic performance in asymmetric hydrogenation of cyclic imines and 2-phenylquinoline

Organometallics

Volumn 25, Issue 10, 2006, Pages 2505-2513

  Yamagata, Tsuneaki ^a   Tadaoka, Hiroshi ^a   Nagata, Mitsuhiro ^a   Hirao, Tsukasa ^a   Kataoka, Yasutaka ^a   Ratovelomanana Vidal, Virginie ^b   Genet, Jean Pierre ^b   Mashima, Kazushi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CARBOXYLATION; CARBOXYLIC ACIDS; CATALYSTS; CHLORIDE MINERALS; COMPLEXATION; HALOGEN COMPOUNDS; HYDROGENATION; SPECTROSCOPIC ANALYSIS; X RAY ANALYSIS;

CHIRAL DIPHOSPHINE COMPLEXES; HALO-CARBOXYLATE IRIDIUM(III) COMPLEXES; OCTAHEDRAL DINUCLEAR STRUCTURES;

IRIDIUM COMPOUNDS;

EID: 33744501305     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om051065j     Document Type: Article

References (53)

1. For comprehensive reviews on asymmetric catalysis: Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer, Berlin, 1999.
3. Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VCH: New York. 2000.
4. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
5. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
6. Genet, J. P. Pure Appl. Chem. 2002, 74, 77.
7. Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
8. (a) Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
9. (b) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
10. (c) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
11. (d) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, K.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
12. (a) Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.
13. (b) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571.
14. Genet, J.-P. Acc. Chem. Res. 2003, 36, 908.
15. Lautens, M.; Fagnou, K. J. Am. Chem. Soc. 2001, 123, 7170.
16. (a) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400.
17. (b) Sablong, R.; Osborn, A. J. Tetrahedron: Asymmetry 1996, 7, 3059.
18. Spindler, F.; Pugin, B.; Blaser, H.-U. Angew. Chem., Int. Ed. Engl. 1990, 29, 558.
19. Spindler, F.; Pugin, B.; Jalett, H.-P.; Buser, H.-P.; Pittelkow, U.; Blaser, H.-U. Chem. Ind. (Dekker) 1996, 68, 153.
20. Blaser, H.-U.; Buser, H.-P.; Haeusel, R.; Jalett, H.-P.; Spindler, F. J. Organomet. Chem. 2001, 621, 34.
21. Pugin, B.; Landert, H.; Spindler, F.; Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 974.
22. Dorta, R.; Egli, P.; Zuercher. F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857.
23. Morimoto, T.; Nakajima, N.; Achiwa, K. Chem. Pharm. Bull. 1994, 42, 1951.
24. Satoh, K.; Inenaga, M.; Kanal, K. Tetrahedron: Asymmetry 1998, 9, 2657.
25. Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425.
26. Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
27. Dorta, R.; Broggini, D.; Stoop, R.; Ruegger, H.; Spindler, F.; Togni, A. Chem. Eur. J. 2004, 10, 267.
28. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem. 1988, 27, 566.
29. Yamagata, T.; Iseki, A.; Tani, K. Chem. Lett. 1997, 12, 1215.
30. Tani, K.; Iseki, A.; Yamagata, T. Angew. Chem., Int. Ed. 1998, 37, 3381.
31. Rosenberg, S.; Mahoney, W. S.; Hayes, J. M.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1986, 5, 1065.
32. Shibata, T.; Yamashita, K.; Ishida, H.; Takagi, K. Org. Lett. 2001, 3, 1217.
33. (a) Tani, K.; Iseki, A.; Yamagata, T. Angew. Chem., Int. Ed. 1998, 37, 3381.
34. (b) Dorta, R.; Togni, A. Organometallics 1998, 17, 3423
35. Mashima, K.; Nakamura, T.; Matsuo, Y.; Tani, K. J. Organomet. Chem. 2000, 607, 51.
36. Ohta, T.; Tonomura, Y.; Nozaki, K.; Takaya, H.; Mashima, K. Organometallics 1996, 15, 1521.
37. For SYNPHOS see: (a) Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P French patent 0112499; PCT FR02/03146, W003029259.
38. (b) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Tetrahedron Lett. 2003, 44, 823.
39. (c) Duprat de Paule, S.; Jeulin, S.; Ratovelo-manana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Eur. J. Org. Chem. 2003, 1931.
40. (d) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Deschaux, G.; Dellis, P. Org. Process. Res. Dev. 2003, 7, 399.
41. (a) Takei, I.; Nishibayashi, Y.; Arikawa, Y.; Uemura S.; Hidai, M. Organametallics 1999, 18, 2271.
42. (b) Willoughby, C. A.; Buchwald, S. L. J. Org. Chem. 1993, 58, 7627.
43. (c) Verdaguer, X.; Lange, U. E. D.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784.
44. (d) Beagley, P.; Davies, P. J.; Blacker, A. J.; White, C. Organometallics 2002, 21, 5852.
45. (a) Herde, J. L.; Lambert, J. C.; Senoff, C. V. Inorg. Synth. 1974, 15, 18.
46. (b) Baghurst, D. R.; Michael, D.; Mingos, P.; Watson, M. J. J. Organomet. Chem. 1989, 368 (3), C43-C45.
47. Hua, D. H.; Miao, S. W.; Bharathi, S. N.; Katuhira, T.; Bravo, A. J. Org. Chem. 1990, 55, 3682.
48. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
49. (a) Ainscough, E. H.; Robinson, S. D.; Levison, J. J. J. Chem. Soc. (A) 1971, 3413.
50. (b) Onderdelinden, A. L.; Ent, A. Inorg. Chim. Acta 1972, 420.
51. (c) Muller, J.; Tschampel, M.; Pickardt, J. Z. Naturforsch. 1986, 41b, 76.
52. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
53. Sheldrick, G. M. SHELX97, Programs for Crystal Structure Analysis (Release 97-2); University of Göttingen, Germany, 1998.