Direct oxidative allylic and vinylic amination of alkenes through selenium catalysis

Angewandte Chemie - International Edition

Volumn 52, Issue 34, 2013, Pages 8952-8956

  Trenner, Johanna ^a   Depken, Christian ^a   Weber, Thomas ^a   Breder, Alexander ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

alkene oxidation; C N coupling; reaction mechanisms; selenium catalysis; synthetic methods

Indexed keywords

C-N COUPLING; CHEMOSELECTIVE; NITROGEN SOURCES; NITROGENATION; REACTION MECHANISM; SYNTHETIC METHODS; TERMINAL OXIDANTS;

AMINES; CATALYSIS; HYDROCARBONS;

SELENIUM;

ALKENE; SELENIUM;

ALKENE OXIDATION; AMINATION; ARTICLE; C N COUPLING; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; REACTION MECHANISMS; SELENIUM CATALYSIS; SYNTHETIC METHODS;

ALKENE OXIDATION; C N COUPLING; REACTION MECHANISMS; SELENIUM CATALYSIS; SYNTHETIC METHODS;

ALKENES; AMINATION; CATALYSIS; OXIDATION-REDUCTION; SELENIUM;

EID: 84882280888     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303662     Document Type: Article

References (77)

1. R. Hili, A. K. Yudin, Nat. Chem. Biol. 2006, 2, 284.
2. Amino Group Chemistry, From Synthesis to the Life Sciences (Ed.:, A. Ricci,), Wiley-VCH, Weinheim, 2008.
3. X.-Y. Liu, P. Gao, Y.-W. Shen, Y.-M. Liang, Org. Lett. 2011, 13, 4196
4. E. J. Yoo, S. Ma, T.-S. Mei, K. S. L. Chan, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7652
5. J. Pan, M. Su, S. L. Buchwald, Angew. Chem. 2011, 123, 8806
6. Angew. Chem. Int. Ed. 2011, 50, 8647
7. Y. Tan, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 3676
8. J. Neumann, S. Rakshit, T. Dröge, F. Glorius, Angew. Chem. 2009, 121, 7024
9. Angew. Chem. Int. Ed. 2009, 48, 6892
10. W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 14560.
11. X. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 10806
12. A. Iglesias, E. G. Pérez, K. Muñiz, Angew. Chem. 2010, 122, 8286
13. Angew. Chem. Int. Ed. 2010, 49, 8109
14. B. Xiao, T.-J. Gong, J. Xu, Z.-J. Liu, L. Liu, J. Am. Chem. Soc. 2011, 133, 1466
15. T. Xiong, Y. Li, L. Mao, Q. Zhang, Q. Zhang, Chem. Commun. 2012, 48, 2246
16. T. Xiong, Y. Lin, Y. Lu, Q. Zhang, Chem. Commun. 2010, 46, 6831
17. K. Sun, Y. Li, T. Xiong, J. Zhang, Q. Zhang, J. Am. Chem. Soc. 2011, 133, 1694
18. Y. Shimizu, Y. Obora, Y. Ishii, Org. Lett. 2010, 12, 1372
19. Á. Iglesias, R. Álvarez, Á. R. de-Lera, K. Muñiz, Angew. Chem. 2012, 124, 2268
20. Angew. Chem. Int. Ed. 2012, 51, 2225
21. K. Muñiz, J. Kirsch, P. Chávez, Adv. Synth. Catal. 2011, 353, 689
22. S. Qiu, T. Xu, J. Zhou, Y. Guo, G. Liu, J. Am. Chem. Soc. 2010, 132, 2856
23. P. A. Sibbald, F. E. Michael, Org. Lett. 2009, 11, 1147.
24. L. S. Hegedus, G. F. Allen, J. J. Bozell, E. L. Waterman, J. Am. Chem. Soc. 1978, 100, 5800.
25. S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172
26. Angew. Chem. Int. Ed. 2002, 41, 164.
27. S. A. Reed, M. C. White, J. Am. Chem. Soc. 2008, 130, 3316
28. S. A. Reed, A. R. Mazzotti, M. C. White, J. Am. Chem. Soc. 2009, 131, 11701.
29. H. J. Kim, J. Kim, S. H. Cho, S. Chang, J. Am. Chem. Soc. 2011, 133, 16382
30. A. A. Kantak, S. Potavathri, R. A. Barham, K. M. Romano, B. DeBoef, J. Am. Chem. Soc. 2011, 133, 19960
31. A. P. Antonchick, R. Samanta, K. Kulikov, J. Lategahn, Angew. Chem. 2011, 123, 8764
32. Angew. Chem. Int. Ed. 2011, 50, 8605
33. S. H. Cho, J. Yoo, S. Chang, J. Am. Chem. Soc. 2011, 133, 5996
34. R. Samanta, J. Lategahn, A. P. Antonchick, Chem. Commun. 2012, 48, 3194.
35. J. A. Souto, D. Zian, K. Muñiz, J. Am. Chem. Soc. 2012, 134, 7242.
36. K. B. Sharpless, T. Hori, L. K. Truesdale, C. O. Dietrich, J. Am. Chem. Soc. 1976, 98, 269.
37. N. Kurose, T. Takahashi, T. Koizumi, J. Org. Chem. 1996, 61, 2932; for representative racemic variants of this approach, see
38. J. E. Fankhauser, R. M. Peevey, P. B. Hopkins, Tetrahedron Lett. 1984, 25, 15-18
39. R. G. Shea, J. N. Fitzner, J. E. Fankhauser, A. Spaltenstein, P. A. Carpino, R. M. Peevey, D. V. Pratt, B. J. Tenge, P. B. Hopkins, J. Org. Chem. 1986, 51, 5243
40. A. Spaltenstein, P. A. Carpino, P. B. Hopkins, Tetrahedron Lett. 1986, 27, 147.
41. F. Chen, C. K. Tan, Y.-Y. Yeung, J. Am. Chem. Soc. 2013, 135, 1232.
42. Organosulfur Chemistry in Asymmetric Synthesis (Eds.:, T. Toru, C. Bolm,), Wiley-VCH, Weinheim, 2008, p.- 197.
43. Organoselenium Chemistry: Synthesis and Reactions (Ed.:, T. Wirth,), Wiley-VCH, Weinheim, 2011
44. F. V. Singh, T. Wirth, in Organoselenium Chemistry (Ed.:, T. Wirth,), Wiley-VCH, Weinheim, 2011, p.- 321
45. T. Wirth, Angew. Chem. 2000, 112, 3890
46. Angew. Chem. Int. Ed. 2000, 39, 3740.
47. B. Chabaud, K. B. Sharpless, J. Org. Chem. 1979, 44, 4204
48. T. Hori, K. B. Sharpless, J. Org. Chem. 1979, 44, 4208.
49. J. A. Tunge, S. R. Mellegaard, Org. Lett. 2004, 6, 1205.
50. A. Toshimitsu, T. Aoai, H. Owada, S. Uemura, M. Okano, J. Org. Chem. 1981, 46, 4727
51. M. Tiecco, L. Testaferri, M. Tingoli, D. Bartoli, Tetrahedron 1989, 45, 6819
52. M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, A. Temperini, Eur. J. Org. Chem. 2000, 3451.
53. J. Wang, J. Chen, C. W. Kee, C.-H. Tan, Angew. Chem. 2012, 124, 2432
54. Angew. Chem. Int. Ed. 2012, 51, 2382.
55. K. L. Rinehart,- Jr., J. B. Gloer, J. C. Cook,- Jr., S. A. Mizsak, T. A. Scahill, J. Am. Chem. Soc. 1981, 103, 1857
56. K. L. Rinehart,- Jr., V. Kishore, K. C. Bible, R. Sakai, D. W. Sullins, K.-M. Li, J. Nat. Prod. 1988, 51, 1.
57. U. Wäspi, D. Blanc, T. Winkler, P. Ruedi, R. Dudler, Mol. Plant-Microbe Interact. 1998, 11, 727
58. U. Wäspi, P. Hassa, A. A. Staempfli, L.-P. Molleyres, T. Winkler, R. Dudler, Microbiol. Res. 1999, 154, 89.
59. M. Oka, Y. Nishiyama, S. Ohta, H. Kamei, M. Konishi, T. Miyaki, T. Oki, H. Kawaguchi, J. Antibiot. 1988, 41, 1331
60. M. Oka, K. Yaginuma, K. Numata, M. Konishi, T. Oki, H. Kawaguchi, J. Antibiot. 1988, 41, 1338.
61. J. Clerc, M. Groll, D. J. Illich, A. S. Bachmann, R. Huber, B. Schellenberg, R. Dudler, M. Kaiser, Proc. Natl. Acad. Sci. USA 2009, 106, 6507
62. A. Baldisserotto, M. Marastoni, R. Gavioli, R. Tomatis, Bioorg. Med. Chem. Lett. 2009, 19, 1966
63. A. Baldisserotto, F. Destro, G. Vertuani, M. Marastoni, R. Gavioli, R. Tomatis, Bioorg. Med. Chem. 2009, 17, 5535
64. M. Marastoni, A. Baldisserotto, S. Cellini, R. Gavioli, R. Tomatis, J. Med. Chem. 2005, 48, 5038
65. J. K. Bang, H. Naka, K. Teruya, S. Aimoto, H. Konno, K. Nosaka, T. Tatsumi, K. Akaji, J. Org. Chem. 2005, 70, 10596.
66. For a recent example of iodine(III)-promoted vinylimide formation, see:, J. A. Souto, P. Becker, Á. Iglesias, K. Muñiz, J. Am. Chem. Soc. 2012, 134, 15505.
67. E. Vedejs, S. Lin, J. Org. Chem. 1994, 59, 1602.
68. M. K. Ghorai, D. P. Tiwari, J. Org. Chem. 2010, 75, 6173
69. W. D. Closson, P. Wriede, S. Bank, J. Am. Chem. Soc. 1966, 88, 1581.
70. R. O. Hutchins, F. Cistone, B. Goldsmith, P. Heuman, J. Org. Chem. 1975, 40, 2018.
71. S. A. Lermontov, S. I. Zavorin, A. N. Pushin, A. N. Chekhlov, N. S. Zefirov, P. J. Stang, Tetrahedron Lett. 1993, 34, 703
72. K. Uneyama, M. Kanai, Tetrahedron Lett. 1990, 31, 3583
73. S. Tomoda, Y. Usuki, Chem. Lett. 1989, 1235
74. J. McCarthy, D. P. Mattheus, C. L. Barney, Tetrahedron Lett. 1990, 31, 973
75. C. Saluzzo, G. Alvernhe, D. Anker, G. Haufe, Tetrahedron Lett. 1990, 31, 663.
76. J. N. Denis, J. Vicens, A. Kief, Tetrahedron Lett. 1979, 20, 2697.
77. For reactions involving similar diselenonium intermediates, see:, M. Tingoli, L. Testaferri, A. Temperini, M. Tiecco, J. Org. Chem. 1996, 61, 7085.