Selective ruthenium-catalyzed alkylation of indoles by using amines

Chemistry - A European Journal

Volumn 16, Issue 9, 2010, Pages 2705-2709

  Imm, Sebastian ^a   Bähn, Sebastian ^a   Tillack, Annegret ^a   Mevius, Kathleen ^a   Neubert, Lorenz ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Alkylation; Amines; Catalysis; Hydrogen transfer; Indoles

Indexed keywords

ALIPHATIC AMINES; CHEMICAL EQUATIONS; HYDROGEN TRANSFER; TRANSFER HYDROGENATIONS;

ALKYLATION; AMINES; CATALYSIS; HYDROCARBONS; RUTHENIUM; TRANSITION METALS;

HYDROGEN;

EID: 77149164745     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903261     Document Type: Article

References (75)

1. a) R. J. Sundberg, Indoles, Academic Press, London, 1996;
2. b) R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970.
3. For reviews about indoles, see: a) K. Krüger, A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2153-2167;
4. b) G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911;
5. c) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2929.
6. a) H. M. Meshram, D. A. Kumar, B. C. Reddy, Helv. Chim. Acta 2009, 92, 1002-1006;
7. b) Y. Hui, Q. Zhang, J. Jiang, L. Lin, X. Liu, X. Feng, J. Org. Chem. 2009, 74, 6878-6880;
8. c) Y. Liu, D. Shang, X. Zhou, X. Liu, X. Feng, Chem. Eur. J. 2009, 15, 2055-2058;
9. d) J.-L. Zhou, M.-C. Ye, X.-L. Sun, Y. Tang, Tetrahedron 2009, 65, 6877-6881;
10. e) Y.-H. Liu, Q.-S. Liu, Z.-H. Zhang, Tetrahedron Lett. 2009, 50, 916-921;
11. f) for interesting reviews, see: g) S-L You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190-2201;
12. h) T. B. Poulsen, K. A. Jorgensen, Chem. Rev. 2008, 108, 2903-2915;
13. i) M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199-1222.
14. S. Whitney, R. Grigg, A. Derrick, A. Keep, Org. Lett. 2007, 9, 3299-3302.
15. For reviews about borrowing hydrogen methodology, see: a) T. D. Nixon, M. K. Whittlesey, J. M. J. Williams, Dalton Trans. 2009, 753-762;
16. b) G. W. Lamb, J. M. J. Williams, Chim. Oggi 2008, 26, 17-19;
17. c) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555-1575;
18. d) G. Guillena, D. J. Ramon, M. Yus, Angew. Chem. 2007, 119, 2410-2416;
19. Angew. Chem. Int. Ed. 2007, 46, 2358-2364.
20. a) O. Saidi, A. J. Blacker, M. M. Farah, S. P. Marsden, J. M. J. Williams, Angew. Chem. 2009, 121, 7511-7514;
21. Angew. Chem. Int. Ed. 2009, 48, 7375-7378;
22. b) M. H. S. A. Hamid, C. L. Allen, G. W. Lamb, A. C. Maxwell, H. C. Maytum, A. J. A. Watson, J. M. J. Williams, J. Am. Chem. Soc. 2009, 131, 1766-1774;
23. c) G. W. Lamb, A. J. A. Watson, K. E. Jolley, A. C. Maxwell, J. M. J. Williams, Tetrahedron Lett. 2009, 50, 3374-3377;
24. d) S. J. Pridmore, P. A. Slatford, A. Daniel, M. K. Whittlesey, J. M. J. Williams, Tetrahedron Lett. 2007, 48, 5115-5120.
25. a) R. Martinez, D. J. Ramon, M. Yus, Org. Biomol. Chem. 2009, 7, 2176-2181;
26. b) R. Martinez, D. J. Ramon, M. Yus, Tetrahedron 2006, 62, 8982-8987;
27. c) R. Martinez, D. J. Ramon, M. Yus, Tetrahedron 2006, 62, 8988-9001;
28. d) R. Martinez, G. J. Brand, D. J. Ramon, M. Yus, Tetrahedron Lett. 2005, 46, 3683-3686.
29. a) R. Yamaguchi, Z. Mingwen, S. Kawagoe, C. Asai, K.-i. Fujita, Synthesis 2009, 1220-1223;
30. b) R. Yamaguchi, S. Kawagoe, C. Asai, K.-i. Fujita, Org. Lett. 2008, 10, 181-184;
31. c) K.-i. Fujita, Y. Enoki, R. Yamaguchi, Tetrahedron 2008, 64, 1943-1954.
32. a) C. Löfberg, R. Grigg, M. A. Whittaker, A. Keep, A. Derrick, J. Org. Chem. 2006, 71, 8023-8027;
33. b) C. Löfberg, R. Grigg, A. Keep, A. Derrick, V. Sridharan, C. Kilner, Chem. Commun. 2006, 5000-5002;
34. c) R. Grigg, T. R. B. Mitchell, S. Sutthivaiyakit, N. Tongpenyai, J. Chem. Soc. Chem. Commun. 1981, 611-612.
35. a) S. Bähn, A. Tillack, S. Imm, K. Mevius, D. Michalik, D. Hollmann, L. Neubert, M. Beller, ChemSusChem 2009, 2, 551-557;
36. b) A. Tillack, D. Hollmann, K. Mevius, D. Michalik, S. Bähn, M. Beller, Eur. J. Org. Chem. 2008, 4745-4750;
37. c) A. Tillack, D. Hollmann, D. Michalik, M. Beller, Tetrahedron Lett. 2006, 47, 8881-8885.
38. a) D. Hollmann, S. Bähn, A. Tillack, R. Parton, R. Altink, M. Beller, Tetrahedron Lett. 2008, 49, 5742-5745;
39. b) D. Hollmann, S. Bähn, A. Tillack, M. Beller, Angew. Chem. 2007, 119, 8440 -8444;
40. Angew. Chem. Int. Ed. 2007, 46, 8291-8294.
41. a) K. Alex, A. Tillack, N. Schwarz, M. Beller, Angew. Chem. 2008, 120, 2337-2340;
42. Angew. Chem. Int. Ed. 2008, 47, 2304 -2307;
43. b) N. Schwarz, A. Pews-Davtyan, D. Michalik, A. Tillack, K. Krüger, A. Torrens, J. L. Diaz, M. Beller, Eur. J. Org. Chem. 2008, 5425-5435;
44. c) K. Alex, N. Schwarz, V. Khedkar, I. A. Sayyed, A. Tillack, D. Michalik, J. Holenz, J. L. Diaz, M. Beller, Org. Biomol. Chem. 2008, 6, 1802-1807;
45. d) I. A. Sayyed, K. Alex, A. Tillack, N. Schwarz, D. Michalik, M. Beller, Eur. J. Org. Chem. 2007, 4525-4528;
46. e) N. Schwarz, A. Pews-Davtyan, K. Alex, A. Tillack, M. Beller, Synthesis 2007, 3722-3730;
47. f) V. Khedkar, A. Tillack, M. Michalik, M. Beller, Tetrahedron 2005, 61, 7622-7631.
48. a) M. H. S. A. Hamid, J. M. J. Williams, Chem. Commun. 2007, 725-727;
49. b) M. H. S. A. Hamid, J. M. J. Williams, Tetrahedron Lett. 2007, 48, 8263-8265.
50. a) C. A. Sandoval, T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, R. Noyori, Chem. Asian J. 2006, 1, 102-110;
51. b) T. Ikariya, K. Murata, R. Noyori, Org. Biomol. Chem. 2006, 4, 393-406;
52. c) S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226-236.
53. D. Hollmann, A. Tillack, D. Michalik, R. Jackstell, M. Beller, Chem. Asian J. 2007, 2, 403-410.
54. For reviews about the Shvo catalyst, see: a) A. Comas-Vives, G. Ujaque, A. Lledós, J. Mol. Struct.: THEOCHEM 2009, 903, 123-132;
55. b) R. Karvembu, R. Prabhakaran, N. Natarajan, Coord. Chem. Rev. 2005, 249, 911-918;
56. c) R. Prabhakaran, Synlett 2004, 2048-2049.
57. a) M. J. Mays, M. J. Morris, P. R. Raithby, Y. Shvo, D. Czarkie, Organometallics 1989, 8, 1162-1167;
58. b) Y. Shvo, D. Czarkie, Y. Rahamim, J. Am. Chem. Soc. 1986, 108, 7400-7402;
59. c) Y. Shvo, R. M. Laine, J. Chem. Soc. Chem. Commun. 1980, 753-754.
60. For highlights on the activation of amines in the a position with subsequent functionalizations, see: a) P. W. Roesky, Angew. Chem. 2009, 121, 4988-4991;
61. Angew. Chem. Int. Ed. 2009, 48, 4892-4894;
62. b) K. Krüger, A. Tillack, M. Beller, ChemSusChem 2009, 2, 715-719.
63. a) J. S. M. Samec, A. H. Ell, J. B. Åberg, T. Privalov, L. Eriksson, J.-E. Bäckvall, J. Am. Chem. Soc. 2006, 128, 14293-14305;
64. b) J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237-248;
65. c) J. B. Åberg, J. S. M. Samec, J.-E. Bäckvall, Chem. Commun. 2006, 2771-2773;
66. d) J. S. M. Samec, L. Mony, J.-E. Bäckvall, Can. J. Chem. 2005, 83, 909-916;
67. e) J. S. M. Samec, A. H. Ell, J.-E. Bäckvall, Chem. Commun. 2004, 2748-2749.
68. a) C. P. Casey, S. E. Beetner, J. B. Johnson, J. Am. Chem. Soc. 2008, 130, 2285-2295;
69. b) C. P. Casey, T. B. Clark, I. A. Guzei, J. Am. Chem. Soc. 2007, 129, 11821-11827;
70. c) C. P. Casey, G. A. Bikzhanova, I. A. Guzei, J. Am. Chem. Soc. 2006, 128, 2286-2293;
71. d) C. P. Casey, G. A. Bikzhanova, Q. Cui, I. A. Guzei, J. Am. Chem. Soc. 2005, 127, 14062-14071;
72. e) C. P. Casey, J. B. Johnson, J. Am. Chem. Soc. 2005, 127, 1883-1894;
73. f) C. P. Casey, J. B. Johnson, S. W. Singer, Q. Cui, J. Am. Chem. Soc. 2005, 127, 3100-3109.
74. Q. He, F. Sun, X. Zheng, S. You, Synlett 2009, 1111-1114.
75. S. Bähn, D. Hollmann, A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2099-2103.