Intermodular FeCl3-catalyzed hydroamination of styrenes

European Journal of Organic Chemistry

Volumn , Issue 16, 2007, Pages 2601-2603

  Michaux, Julien ^a   Terrasson, Vincent ^b   Marque, Sylvain ^b   Wehbe, Johny ^c   Prim, Damien ^b   Campagne, Jean Marc ^c  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^c INSTITUT CHARLES GERHARDT   (France)

Author keywords

Hydroamination; Iron; Styrenes

Indexed keywords

EID: 34250624527     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.10027ejoc.200700023     Document Type: Article

References (30)

1. Reviews: a) T. Müller, M. Beller, Chem. Rev. 1998, 98, 675-704;
2. b) M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368-3398;
3. c) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935-946;
4. d) J. J. Brunet, D. Neibecker in Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, pp. 91-141.
5. For a recent review on catalytic and asymmetric hydroamination of nonactivated olefins, see: a) K. C. Hultzsch, Org. Biomol. Chem. 2005, 3, 1819-1824;
6. b) for a recent example, see: J. Collin, O. Jacquet, E. Schulz, A. Trifonov, Chem. Eur. J. 2005, 11, 3455-3462.
7. For recent Pd, Pt, Ti and Fe-catalyzed intramolecular hydroaminations reactions, see: a) E. M. Forrest, B. M. Cochran, J. Am. Chem. Soc. 2006, 128, 4246-4247;
8. b) C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070-1071;
9. c) C. Muller, C. Loos, N. Schulenberg, S. Doye, Eur. J. Org. Chem. 2006, 2499-2503;
10. d) K. Komeyama, T. Morimoto, T. Takaki, Angew. Chem. Int. Ed. 2006, 45, 2938-2941.
11. Intramolecular proton-catalyzed hydroamination has been reported twice, see: a) B. Schlummer, J. F. Hartwig, Org. Lett. 2002, 4, 1471-1474;
12. b) M. Beller, O. R. Thiel, H. Trautwein, Synlett 1999, 243-245.
13. L. L. Anderson, J. Arnold, R. G. Bergman, J. Am. Chem. Soc. 2005, 127, 14542-14543.
14. During the submission of this article, a related paper dealing with the hydroamination of styrenes in the presence of a copper catalyst has appeared in the literature. See J. G. Taylor, N. Whittall, K. K. Hii, Org. Lett. 2006, 8, 3561-3564.
15. a) M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546-9547;
16. b) U. Nettekoven, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1166-1167;
17. c) J. F. Hartwig, Pure Appl. Chem. 2004, 76, 507-516;
18. d) L. K. Vo, D. A. Singleton, Org. Lett. 2004, 6, 2469-2472.
19. T. Minami, H. Okamoto, S. Ikeda, R. Tanaka, F. Ozawa, M. Yoshijufi, Angew. Chem. Int. Ed. 2001, 40, 4501-4503.
20. a) M. Utsunomiya, R. Kuwano, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 5608-5609;
21. b) M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 2702-2703.
22. H. Qian, R. A. Widenhoefer, Org. Lett. 2005, 7, 2635-2638.
23. J. Zhang, C. Yang, C. He, J. Am. Chem. Soc. 2006, 128, 1798-1799.
24. X. Liu, C. Li, C. Che, Org. Lett. 2006, 8, 2707-2710.
25. a) L. Keller, M. Vargas-Sanchez, D. Prim, F. Couty, G. Evano, J. Marrot, J. Organomet. Chem. 2005, 690, 2306-2311;
26. b) F. Couty, G. Evano, D. Prim, J. Marrot, Eur. J. Org. Chem. 2004, 3893-3897.
27. V. Terrasson, S. Marque, M. Georgy, D. Prim, J.-M. Campagne, Adv. Synth. Catal. 2006, 348, 2063-2067.
28. [10].
29. III-catalyzed hydroarylation of styrenes, see: J. Ki-chel, I. Jovel, K. Mertins. A. Zapf, M. Beller, Org. Lett. 2006, 8, 19-22.
30. A commercial mixture of 1-(chloromethyl)4-vinylbenzene and 1-(chloromethyl)-3-vinylbenzene was used in this reaction.