Hydrogenation of quinolines using a recyclable phosphine-free chiral cationic ruthenium catalyst: Enhancement of catalyst stability and selectivity in an ionic liquid

Angewandte Chemie - International Edition

Volumn 47, Issue 44, 2008, Pages 8464-8467

  Zhou, Haifeng ^a,c   Li, Zhiwei ^a   Wang, Zhijian ^a   Wang, Tianli ^a   Xu, Lijin ^b   He, Yanmei ^a   Fan, Qing Hua ^a   Pan, Jie ^a   Gu, Lianquan ^c   Chan, Albert S C ^b  

^a PEKING UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^c SUN YAT SEN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Hydrogenation; Ionic liquids; Quinolines

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; CHEMICAL REACTIONS; CHEMICAL REACTIVITY; ENANTIOSELECTIVITY; HYDROGENATION; IONIZATION OF LIQUIDS; IONS; PHOSPHORUS COMPOUNDS; RUTHENIUM;

ASYMMETRIC CATALYSIS; CATALYST RECYCLING; CATALYST STABILITIES; CHEMICAL EQUATIONS; LIQUID ASSETS; QUINOLINES; RUTHENIUM CATALYSTS;

IONIC LIQUIDS;

IONIC LIQUID; PHOSPHINE; PHOSPHINE DERIVATIVE; QUINOLINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; HYDROGENATION;

CATALYSIS; HYDROGENATION; IONIC LIQUIDS; PHOSPHINES; QUINOLINES; RUTHENIUM;

EID: 54249139518     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802237     Document Type: Article

References (67)

1. a) T. Welton, Chem. Rev. 1999, 99, 2071;
2. b) P. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926;
3. Angew. Chem. Int. Ed. 2000, 39, 3772;
4. c) J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667;
5. d) T. Welton, Coord. Chem. Rev. 2004, 248, 2459;
6. e) V. I. Pârvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615;
7. f) C. E. Song, Chem. Commun. 2004, 1033;
8. g) J. Durand, E. Teuma, M. Gómez, C. R. Chim. 2007, 10, 152.
9. For review, see: a) C. E. Song, M. Y. Yoon, D. S. Choi, Bull. Korean Chem. Soc. 2005, 26, 1321.
10. For recent examples, see: b) C. E. Song, D. Jung, S. Y. Choung, E. J. Roh, S.-G. Lee, Angew. Chem. 2004, 116, 6309;
11. Angew. Chem. Int. Ed. 2004, 43, 6183;
12. c) J. Mo, L. Xu, J. Xiao, J. Am. Chem. Soc. 2005, 127, 751;
13. d) X. Mu, J. Meng, Z. Li, Y. Kou, J. Am. Chem. Soc. 2005, 127, 9694;
14. e) C. Daguenet, P. J. Dyson, Organometallics 2006, 25, 5811;
15. f) K. Takahashi, H. Nakano, R. Fujita, Chem. Commun. 2007, 263.
16. For selected examples of asymmetric hydrogenation in ionic liquids, see: a) A. L. Monteiro, F. K. Zinn, R. F. de Souza, J. Dupont, Tetrahedron: Asymmetry 1997, 8, 177;
17. b) R. A. Brown, P. Pollet, E. C. McKoon, A. Eckert, C. L. Liotta, P. G. Jessop, J. Am. Chem. Soc. 2001, 123, 1254;
18. c) S. Guernik, A. Wolfson, M. Herskowitz, N. Greenspoon, S. Geresh, Chem. Commun. 2001, 2314;
19. d) A. Hu, H. Ngo, W. Lin, Angew. Chem. 2004, 116, 2555;
20. Angew. Chem. Int. Ed. 2004, 43, 2501;
21. e) M. Solinas, A. Pfaltz, P. G. Cozzi, W. Leitner, J. Am. Chem. Soc. 2004, 126, 16142;
22. f) R. Giernoth, M. S. Krumm, Adv. Synth. Catal. 2004, 346, 989;
23. g) H. Wong, Y. H. See-Toh, F. C. Ferreira, R. Crook, A. G. Livingston, Chem. Commun. 2006, 2063.
24. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
25. b) G. Q. Lin, Y. M. Li, A. S. C. Chan, Principles and Applications of Asymmetric Synthesis, Wiley, New York, 2001.
26. For recent reviews, see: a) F. Glorius, Org. Biomol. Chem. 2005, 3, 4171;
27. b) Y. G. Zhou, Acc. Chem. Res. 2007, 40, 1357,
28. for selected examples, see: c) C. Legault, A. Charette, J. Am. Chem. Soc. 2005, 127, 8966;
29. d) R. Kuwano, M. Kashiwabara, Org. Lett. 2006, 8, 2653;
30. e) S. M. Lu, Y. Q. Wang, X. W. Han, Y. G. Zhou, Angew. Chem. 2006, 118, 2318;
31. Angew. Chem. Int. Ed. 2006, 45, 2260;
32. f) S. Kaiser, S. P. Smidt, A. Pfaltz, Angew. Chem. 2006, 118, 5318;
33. Angew. Chem. Int. Ed. 2006, 45, 5194;
34. g) R. Kuwano, M. Kashiwabara, M. Ohsumi, H. Kusano, J. Am. Chem. Soc. 2008, 130, 808.
35. For recent examples, see: a) W. B. Wang, S. M. Lu, P. Y. Yang, X. W. Han, Y. G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536;
36. b) L. Xu, K. Lam, J. Ji, J. Wu, Q. H. Fan, W. H. Lo, A. S. C. Chan, Chem. Commun. 2005, 1390;
37. c) M. T. Reetz, X. Li, Chem. Commun. 2006, 2159;
38. d) W. J. Tang, S. F. Zhu, L. J. Xu, Q. L. Zhou, Q. H. Fan, H. F. Zhou, K. Lam, A. S. C. Chan, Chem. Commun. 2007, 613;
39. e) Z. J. Wang, G. J. Deng, Y. Li, Y. M. He, W. J. Tang, Q. H. Fan, Org. Lett. 2007, 9, 1243.
40. For asymmetric transfer hydrogenation of quinolines with organocatalysts, see: a) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765;
41. Angew. Chem. Int. Ed. 2006, 45, 3683;
42. b) Q. S. Guo, D. M. Du, J. Xu, Angew. Chem. 2008, 120, 771;
43. Angew. Chem. Int. Ed. 2008, 47, 759.
44. For selected examples of phosphine-free catalysts used for homogeneous hydrogenation reactions, see: a) C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8952;
45. b) M. T. Powell, D. Hou, M. C. Perry, X. Cui, K. Burgess, J. Am. Chem. Soc. 2001, 123, 8878;
46. c) M. Ito, M. Hirakawa, K. Murata, T. Ikariya, Organometallics 2001, 20, 379;
47. d) H. Guan, M. Iimura, M. P. Magee, J. R. Norton, G. Zhu, J. Am. Chem. Soc. 2005, 127, 7805;
48. e) C. Hedberg, K. Källström, P. I. Arvidsson, P. Brandt, P. G. Andersson, J. Am. Chem. Soc. 2005, 127, 15083;
49. f) H. Huang, T. Okuno, K. Tsuda, M. Yoshimura, M. Kitamura, J. Am. Chem. Soc. 2006, 128, 8716.
50. a) T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724;
51. b) C. a Sandoval, T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, R. Noyori, Chem. Asian J. 2006, 1, 102;
52. c) T. Ohkuma, K. Tsutsumi, N. Utsumi, N. Arai, R. Noyori, K. Murata, Org. Lett. 2007, 9, 255.
53. a) Q. H. Fan, Y. M. Li, A. S. C. Chan, Chem. Rev. 2002, 102, 3385;
54. b) K. H. Lam, L. Xu, L. Feng, J. Ruan, Q. Fan, A. S. C. Chan, Can. J. Chem. 2005, 83, 903;
55. c) H. F. Zhou, Q. H. Fan, W. J. Tang, L. J. Xu, Y. M. He, G. J. Deng, L. W. Zhao, L. Q. Gu, A. S. C. Chan, Adv. Synth. Catal. 2006, 348, 2172.
56. For solvent-induced reversal of enantioselectivity, see: a) S. Arseniyadis, A. Valleix, A. Wagner, C. Mioskowski, Angew. Chem. 2004, 116, 3376;
57. Angew. Chem. Int. Ed. 2004, 43, 3314;
58. b) J. Zhou, M. Ye, Z. Huang, Y. Tang, J. Org. Chem. 2004, 69, 1309.
59. Similar observations were made for Rh- and Ir-catalysts in the asymmetric hydrogenation reactions; see Refs. [3c] and [3e].
60. a) J. L. Anderson, J. Ding, T. Welton, D. W. Armstrong, J. Am. Chem. Soc. 2002, 124, 14247;
61. b) C. Sievers, O. Jimenez, T. E. Müller, S. Steuernagel, J. A. Lercher, J. Am. Chem. Soc. 2006, 128, 13990.
62. J. L. Anthony, E. J. Maginn, J. F. Brennecke, J. Phys. Chem. B 2002, 106, 7315.
63. When toluene was used as a co-solvent for the hydrogenation of 2n under otherwise identical reaction conditions, similar chemoselectivity and enantioselectivity was observed but a slightly lower conversion into 3n was obtained (72% yield, 96% ee, and 24% starting material).
64. W. C. Chan, C. P. Lau, Y. Z. Chen, Y. Q. Fang, S. M. Ng, Organometallics 1997, 16, 34.
65. As expected, hydrogenation of 3-methylquinoline catalyzed by (S,S)-1a in ionic liquid gave a racemic mixture of products. See the Supporting Information for details.
66. M. Rueping, T. Theissmann, S. Raja, J. W. Bats, Adv. Synth. Catal. 2008, 350, 1001.
67. For a recent review on catalytic ionic hydrogenation, see: R. M. Bullock, Chem. Eur. J. 2004, 10, 2366.