Inhibiting deactivation of iridium catalysts with bulky substituents on coordination atoms

Tetrahedron Letters

Volumn 51, Issue 3, 2010, Pages 525-528

  Wang, Duo Sheng ^a   Zhou, Juan ^b   Wang, Da Wei ^a   Guo, Yin Long ^b   Zhou, Yong Gui ^a,b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; IRIDIUM; PHOSPHORUS; QUINOLINE DERIVATIVE;

ARTICLE; ATOM; CATALYSIS; CATALYST; HYDROGENATION; REACTION ANALYSIS;

EID: 71649102649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.075     Document Type: Article

References (62)

1. For reviews on Ir-catalyzed asymmetric hydrogenation, see:. Pfaltz A., Blankenstein J., Hilgraf R., Hörmann E., Mclntyre S., Menges F., Schönleber M., Smidt S.P., Wüstenberg B., and Zimmermann N. Adv. Synth. Catal. 345 (2003) 33-43
2. Cui X., and Burgess K. Chem. Rev. 105 (2005) 3272-3296
3. Källström K., Munslow I., and Andersson P.G. Chem. Eur. J. 12 (2006) 3194-3200
4. Crabtree R. Acc. Chem. Res. 12 (1979) 331-337
5. Wang H.-H., Casalnuovo A.L., Johnson B.J., Mueting A.M., and Pignolet L.H. Inorg. Chem. 27 (1988) 325-331
6. Blaser H.-U., Pugin B., Spindler F., and Togni A.C.R. Chimie 5 (2002) 379-385
7. Smidt S.P., and Pfaltz A. Organometallics 22 (2003) 1000-1009
8. Martínez-Viviente E., and Pregosin P.S. Inorg. Chem. 42 (2003) 2209-2214
9. Dervisi A., Carcedo C., and Ooi L.-L. Adv. Synth. Catal. 348 (2006) 175-183
10. Heller D., de Vries A.H.M., and de Vries J.G. In: de Vries J.G., and Elsevier C.J. (Eds). Handbook of Homogeneous Hydrogenation (2007), Wiley-VCH Publishers, Weinheim
11. Xu Y., Celik M.A., Thompson A.L., Cai H., Yurtsever M., Odell B., Green J.C., Mingos D.M.P., and Brown J.M. Angew. Chem., Int. Ed. 48 (2009) 582-585
12. Lightfoot A., Schnider P., and Pfaltz A. Angew. Chem., Int. Ed. 37 (1998) 2897-2899
13. Drago D., Pregosin P.S., and Pfaltz A. Chem. Commun. (2002) 286-287
14. Smidt S.P., Zimmermann N., Studer M., and Pfaltz A. Chem. Eur. J. 10 (2004) 4685-4693
15. Wüstenberg B., and Pfaltz A. Adv. Synth. Catal. 350 (2008) 174-178
16. Schönleber M., Hilgraf R., and Pfaltz A. Adv. Synth. Catal. 350 (2008) 2033-2038
17. Pugin B., Landert H., Spindler F., and Blaser H.-U. Adv. Synth. Catal. 344 (2002) 974-979
18. Liu G.H., Yao M., Wang J.Y., Lu X.Q., Liu M.M., Zhang F., and Li H.X. Adv. Synth. Catal. 350 (2008) 1464-1468
19. Wang Z.-J., Deng G.-J., Li Y., He Y.-M., Tang W.-J., and Fan Q.-H. Org. Lett. 9 (2007) 1243-1246
20. Zhu S.-F., Xie J.-B., Zhang Y.-Z., Li S., and Zhou Q.-L. J. Am. Chem. Soc. 128 (2006) 12886-12891
21. Tang W.-J., Zhu S.-F., Xu L.-J., Zhou Q.-L., Fan Q.-H., Zhou H.-F., Lam K., and Chan A.S.C. Chem. Commun. (2007) 613-615
22. Xu Y., Mingos D.M.P., and Brown J.M. Chem. Commun. (2008) 199-201
23. For recent reviews on hydrogenation of aromatic compounds, see:. Glorius F. Org. Biomol. Chem. 3 (2005) 4171-4175
24. Lu S.-M., Han X.-W., and Zhou Y.-G. Chin. J. Org. Chem. 25 (2005) 634-640
25. Dyson P.J. Dalton Trans. (2003) 2964-2974
26. Zhou Y.-G. Acc. Chem. Res. 40 (2007) 1357-1366
27. Kuwano R. Hetereocycles 76 (2008) 909-922
28. For our group's work on asymmetric hydrogenation of quinolines, see:. Wang W.-B., Lu S.-M., Yang P.-Y., Han X.-W., and Zhou Y.-G. J. Am. Chem. Soc. 125 (2003) 10536-10537
29. Lu S.-M., Han X.-W., and Zhou Y.-G. Adv. Synth. Catal. 346 (2004) 909-912
30. Yang P.-Y., and Zhou Y.-G. Tetrahedron: Asymmetry 15 (2004) 1145-1149
31. Lu S.-M., Wang Y.-Q., Han X.-W., and Zhou Y.-G. Angew. Chem., Int. Ed. 45 (2006) 2260-2263
32. Zhao Y.-J., Wang Y.-Q., and Zhou Y.-G. Chin. J. Catal. 26 (2005) 737-739
33. Wang D.-W., Zeng W., and Zhou Y.-G. Tetrahedron: Asymmetry 18 (2007) 1103-1107
34. Lu S.-M., Han X.-W., and Zhou Y.-G. J. Organomet. Chem. 692 (2007) 3065-3069
35. Wang X.-B., and Zhou Y.-G. J. Org. Chem. 73 (2008) 5640-5642
36. Wang D.-W., Wang X.-B., Wang D.-S., Lu S.-M., Zhou Y.-G., and Li Y.-X. J. Org. Chem. 74 (2009) 2780-2787
37. For other groups' work on metal catalyzed asymmetric hydrogenation of quinolines, see:. Xu L.J., Lam K.H., Ji J.X., Wu J., Fan Q.-H., Lo W.-H., and Chan A.S.C. Chem. Commun. (2005) 1390-1392
38. Lam K.H., Xu L.J., Feng L.C., Fan Q.-H., Lam F.L., Lo W.-H., and Chan A.S.C. Adv. Synth. Catal. 347 (2005) 1755-1758
39. Wu J., and Chan A.S.C. Acc. Chem. Res. 39 (2006) 711-720
40. Chan S.-H., Lam K.-H., Li Y.-M., Xu L.-J., Tang W.-J., Lam F.-L., Lo W.-H., Yu W.-Y., Fan Q.-H., and Chan A.S.C. Tetrahedron: Asymmetry 18 (2007) 2625-2631
41. Reetz M.T., and Li X.-G. Chem. Commun. (2006) 2159-2160
42. Qiu L., Kwong F.Y., Wu J., Lam W.H., Chan S., Yu W.-Y., Li Y.-M., Guo R., Zhou Z., and Chan A.S.C. J. Am. Chem. Soc. 128 (2006) 5955-5965
43. Li Z.-W., Wang T.-L., He Y.-M., Wang Z.-J., Fan Q.-H., Pan J., and Xu L.-J. Org. Lett. 10 (2008) 5265-5268
44. Zhou H.-F., Li Z.-W., Wang Z.-J., Wang T.-L., Xu L.-J., He Y.-M., Fan Q.-H., Pan J., Gu L.-Q., and Chan A.S.C. Angew. Chem., Int. Ed. 47 (2008) 8464-8467
45. Lu S.-M., and Bolm C. Adv. Synth. Catal. 350 (2008) 1101-1105
46. Mršić N., Lefort L., Boogers J.A.F., Minnaard A.J., Feringa B.L., and de Vries J.G. Adv. Synth. Catal. 350 (2008) 1081-1089
47. Yamagata T., Tadaoka H., Nagata M., Hirao T., Kataoka Y., Ratovelomanana-Vidal V., Genet J.P., and Mashima K. Organometallics 25 (2006) 2505-2513
48. Jahjah M., Alame M., Pellet-Rostaing S., and Lemaire M. Tetrahedron: Asymmetry 18 (2007) 2305-2312
49. Deport C., Buchotte M., Abecassis K., Tadaoka H., Ayad T., Ohshima T., Genet J.-P., Mashima K., and Ratovelomanana-Vidal V. Synlett (2007) 2743-2747
50. Fache F. Synlett (2004) 2827-2829
51. Fujita K.-I., Kitatsuji C., Furukawa S., and Yamaguchi R. Tetrahedron Lett. 45 (2004) 3215-3217
52. Eggenstein M., Thomas A., Theuerkauf J., Franciò G., and Leitner W. Adv. Synth. Catal. 351 (2009) 725-732
53. Wang C., Li C.Q., Wu X.F., Pettman A., and Xiao J.L. Angew. Chem., Int. Ed. 48 (2009) 6524-6528
54. Tadaoka H., Cartigny D., Nagano T., Gosavi T., Ayad T., Genet J.-P., Ohshima T., Ratovelomanana-Vidal V., and Mashima K. Chem. Eur. J. 15 (2009) 9990-9994
55. Wang Z.-J., Zhou H.-F., Wang T.-L., He Y.-M., and Fan Q.-H. Green Chem. 11 (2009) 767-769
56. For the work on organocatalytic asymmetric hydrogenation of quinolines, see:. Rueping M., Antonchick A.P., and Theissmann T. Angew. Chem., Int. Ed. 45 (2006) 3683-3686
57. Rueping M., Theissmann T., and Antonchick A.P. Synlett (2006) 1071-1074
58. Rueping M., Theissmann T., Raja S., and Bats J.W.P. Adv. Synth. Catal. 350 (2008) 1001-1006
59. Guo Q.-S., Du D.-M., and Xu J. Angew. Chem., Int. Ed. 47 (2008) 759-762
60. You S.-L. Chem. Asian J. 2 (2007) 820-827
61. Guo H., Qian R., Liao Y., Ma S., and Guo Y. J. Am. Chem. Soc. 127 (2005) 13060-13064
62. Bao H., Zhou J., Wang Z., Guo Y., You T., and Ding K. J. Am. Chem. Soc. 130 (2008) 10116-10127