A simple and efficient iron-catalyzed intramolecular hydroamination of unactivated olefins

Angewandte Chemie - International Edition

Volumn 45, Issue 18, 2006, Pages 2938-2941

  Komeyama, Kimihiro ^a   Morimoto, Takayuki ^a   Takaki, Ken ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Alkenes; Homogeneous catalysis; Hydroamination; Iron; Nitrogen heterocycles

Indexed keywords

AMINOOLEFINS; HOMOGENEOUS CATALYSIS; HYDROAMINATION; NITROGEN HETEROCYCLES;

ACTIVATION ANALYSIS; AIR; CATALYST ACTIVITY; IRON; MOISTURE; REACTION KINETICS;

OLEFINS;

ALKENE; COPPER; HYDROGEN; IRON; LIGAND; SOLVENT;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DEUTERIUM HYDROGEN EXCHANGE; KINETICS;

ALKENES; AMINATION; CATALYSIS; COPPER; DEUTERIUM EXCHANGE MEASUREMENT; HYDROGEN; IRON; KINETICS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLVENTS;

EID: 33746216342     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503789     Document Type: Article

References (73)

1. D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435-446.
2. For reviews on inter- and intramolecular hydroaminations, see: a) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159;
3. b) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114;
4. c) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703;
5. for a selected example of o-iodoxybenzoic acid (IBX) mediated hydroamination, see: d) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629;
6. Angew. Chem. Int. Ed. 2000, 39, 2525-2529;
7. for recent examples of Brønsted acid catalyzed hydroamination, see: e) B. Schlummer, J. F. Hartwig, Org. Lett. 2002, 4, 1471-1474;
8. f) C. M. Haskins, D. W. Knight, Chem. Commun. 2002, 2724-2725;
9. for a selected example of N-bromosuccinimide-catalyzed hydroamination, see: g) S. K. Talluri, A. Sudalai, Org. Lett. 2005, 7, 855-857.
10. Ca: a) M. R. Crimmin, I. J. Casely, M. S. Hill, J. Am. Chem. Soc. 2005, 127, 2042-2043;
11. lanthanides: b) K. C. Hultzsch, Org. Biomol. Chem. 2005, 3, 1819-1824;
12. c) T. K. Panda, A. Zulys, M. T. Gamer, P. W. Roesky, Organometallics 2005, 24, 2197-2202;
13. d) J. Collin, J.-C. Daran, O. Jacquet, E. Schulz, A. Trifonov, Chem. Eur. J. 2005, 11, 3455-3462;
14. e) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673-686;
15. f) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560-9561;
16. g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797-3799;
17. Angew. Chem. Int. Ed. 2002, 41, 3645-3647;
18. actinides: h) T. Straub, A. Haskel, T. G. Neyroud, M. Kapon, M. Botoshansky, M. S. Eisen, Organometallics 2001, 20, 5017-5035;
19. i) A. Haskel, T. Straub, M. S. Eisen, J. Am. Chem. Soc. 1996, 118, 3773-3775;
20. Sc: j) J. Y. Kim, T. Livinghouse, Org. Lett. 2005, 7, 4391-4393;
21. Group 4 metals: k) J. A. Bexrud, J. D. Beard, D. C. Leitch, L. L. Schafer, Org. Lett. 2005, 7, 1959-1962;
22. l) D. V. Gribkov, K. C. Hultzsch, Angew. Chem. 2004, 116, 5659-5663;
23. Angew. Chem. Int. Ed. 2004, 43, 5542-5546;
24. m) A. Tillack, H. Jiao, I. G. Castro, C. G. Hartung, M. Beller, Chem. Eur. J. 2004, 10, 2409-2420;
25. n) L. Ackermann, R. G. Bergman, R. N. Roy, J. Am. Chem. Soc. 2003, 125, 11 956-11 963;
26. o) F. Pohlki, S. Doye, Angew. Chem. 2001, 113, 2361-2364;
27. Angew. Chem. Int. Ed. 2001, 40, 2305-2308;
28. p) B. F. Straub, R. G. Bergman, Angew. Chem. 2001, 113, 4768-4771;
29. Angew. Chem. Int. Ed. 2001, 40, 4632-4635;
30. q) P. L. McGrane, M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1992, 114, 5459-5460;
31. r) P. J. Walsh, A. M. Baranger, R. G. Bergman, J. Am. Chem. Soc. 1992, 114, 1708-1719.
32. R. Anwander in Lanthanides: Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer, New York, 1999, pp. 1-61.
33. Pd: a) M. Meguro, Y. Yamamoto, Tetrahedron Lett. 1998, 39, 5421-5424;
34. Ag: b) T. Gallagher, S, W. Jones, M. F. Mahon, K. C. Molloy, J. Chem. Soc. Perkin Trans. 1 1991, 2193-2198;
35. c) J. S. Prasad, L. S. Liebeskind, Tetrahedron Lett. 1988, 29, 4253-4256;
36. d) R. Kinsman, D. Lathbury, P. Vernon, T. Gallagher, J. Chem. Soc. Chem. Commun. 1987, 243-244;
37. e) D. Lathbury, T. Gallagher, J. Chem. Soc. Chem. Commun. 1986, 114-115;
38. f) S. Arseniyadis, J. Sartoretti, Tetrahedron Lett. 1985, 26, 729-732;
39. g) S. Arseniyadis, J, Gore, Tetrahedron Lett. 1983, 37, 3997-4000;
40. h) A. Claesson, C. Sahlberg, K. Luthman, Acta Chem. Scand. Ser. B 1979, 33, 309-310.
41. Pd: a) G. B. Bajracharya, Z. Huo, Y. Yamamoto, J. Org. Chem. 2005, 70, 4883-4886;
42. b) N. T. Patil, N. K. Pahadi, Y. Yamamoto, Tetrahedron Lett. 2005, 46, 2101-2103;
43. c) L. M. Letete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 1622-1623;
44. d) T. E. Müller, M. Berger, M. Grosche, E. Herdtweck, F. P. Schmidtchen, Organometallics 2001, 20, 4384-4393;
45. e) T. E. Müller, A.-K. Pleier, J. Chem. Soc. Dalton Trans. 1999, 583-587;
46. f) T. E. Müller, Tetrahedron Lett. 1998, 39, 5961-5962;
47. Rh and Ir: g) L. D. Field, B. A. Messerle, K. Q. Vuong, P. Turner, Organometallics 2005, 24, 4241-4250;
48. Re: h) L. L. Ouh, T. E. Müller, Y. K. Yan, J. Organomet. Chem. 2005, 690, 3774-3782;
49. Cu: i) Y. Tamaru, M. Kimura, S. Tanaka, S. Kure, Z.-I. Yoshida, Bull. Chem. Soc. Jpn. 1994, 67, 2838-2849.
50. L. S. Hegedus, J. M. McKearin, J. Am. Chem. Soc. 1982, 104, 2444-2451.
51. a) R. F. Shannon, L. B. Jodie, S. S. Stahl, Angew. Chem. 2002, 114, 172-174;
52. Angew. Chem. Int. Ed. 2002, 41, 164-166;
53. b) P. J. Harrington, L. S. Hegedus, K. F. McDaniel, J. Am. Chem. Soc. 1987, 109, 4335-4338;
54. c) L. S. Hegedus, B. Akermark, K. Zetterberg, L. F. Olsson, J. Am. Chem. Soc. 1984, 106, 7122-7126;
55. d) L. S. Hegedus, J. M. McKearin, J. Am. Chem. Soc. 1982, 104, 2444-2451;
56. e) L. S. Hegedus, G. F. Allen, D. J. Olsen, J. Am. Chem. Soc. 1980, 102, 3583-3587;
57. f) L. S. Hegedus, G. F. Allen, J. J. Bozell, E. L. Waterman, J. Am. Chem. Soc. 1978, 100, 5800-5807;
58. g) L. S. Hegedus, G. F. Allen, E. L. Waterman, J. Am. Chem. Soc. 1976, 98, 2674-2676.
59. C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070-1071.
60. a) L. S. Hegedus in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, pp. 551-569;
61. b) A. J. Pearson in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, pp. 663-714;
62. c) A. Rosan, M. J. Rosenblum, J. Org. Chem. 1975, 40, 3621-3622.
63. a) S. R. Berryhill, T. Price, M. Rosan, J. Org. Chem. 1983, 48, 158-162;
64. b) P. Lennon, M. Madhavarao, A. Rosan, J. Organomet. Chem. 1976, 108, 93-109.
65. For a review on iron-catalyzed reactions, see: C. Bolm, J. Legros, J. L. Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254.
66. 2, the terminal olefinic moiety of 1a was isomerized to an internal one.
67. a) J.-S. Ryu, T. J. Marks, Org. Lett. 2001, 3, 3091-3094;
68. b) B. Åkermark, K. Zetterberg, J. Am. Chem. Soc. 1984, 106, 5560-5561;
69. c) B. Åkermark, J.-E. Bäckvall, Tetrahedron Lett. 1975, 16, 819-822.
70. [2f]
71. a) T. C. Wabnitz, J.-Q. Yu, J. B. Spencer, Chem. Eur. J. 2004, 10, 484-493;
72. b) P. V. Bonnesen, C. L. Puckett, R. V. Honeychuck, W. H. Hersh, J. Am. Chem. Soc. 1989, 111, 6070-6081.
73. No reaction was observed with other acid catalysts such as p-toluenesulfinic acid and phenylacetic acid.