Palladium-catalyzed amination of 1-bromo- and 1-chloro-1,3-butadienes: A general method for the synthesis of 1-amino-1,3-butadienes

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1697-1701

  Barluenga, José ^a   Aznar, Fernando ^a   Moriel, Patricia ^a   Valdés, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Amination; Aminodiene; Cross coupling; Enamine; Palladium

Indexed keywords

1,3 BUTADIENE; ALIPHATIC AMINE; ALKADIENE; AMINE; AROMATIC AMINE; LIGAND; METAL; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 12344327366     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404201     Document Type: Article

References (37)

1. a) The Chemistry of Enamines, (Ed.: Z. Rappaport), Wiley, New York, 1994;
2. b) Enamines: Synthesis, Structure and Reactions, 2nd edn., (Ed.: A. G. Cook), Marcel Dekker, New York, 1998.
3. For reviews on Diels-Alder reactions of amino-substituted dienes, see: a) D. Enders, O. Meyer, Liebigs Ann. 1996, 1023-1035; b) J. Barluenga, A. Suárez-Sobrino, L-A. López, Aldrichimica Acta 1999, 32, 4-15.
4. For reviews on Diels-Alder reactions of amino-substituted dienes, see: a) D. Enders, O. Meyer, Liebigs Ann. 1996, 1023-1035; b) J. Barluenga, A. Suárez-Sobrino, L-A. López, Aldrichimica Acta 1999, 32, 4-15.
5. L. E. Overman, G. F. Taylor, K. N. Houk, L. N. Domelsmith, J. Am. Chem. Soc. 1978, 100, 3182.
6. a) S. A. Kozmin, V. H. Rawal, J. Am. Chem. Soc. 1997, 119, 7165-7166;
7. b) R. Robiette, K. Cheboub-Benchaba, D. Peeters, J. Marchand-Brynaert, J. Org. Chem. 2003, 68, 9809-9812 and references cited therein.
8. P. Wipf, X. Wang, Tetrahedron Lett. 2000, 41, 8747-8751.
9. a) L. E. Overman, P. J. Jessup, J. Am. Chem. Soc. 1978, 100, 5179;
10. b) S. A. Kozmin, T. Iwama, Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 4628-4641.
11. For reviews on the synthesis and reactivity dienamines, see: a) P. W. Hickmott, Tetrahedron 1984, 40, 2989-3051; b) O. Cervinka, in: The Chemistry of Enamines, Part 1, (Ed.: Z. Rappoport), Wiley, New York, 1994, chap. 9, p. 467.
12. For reviews on the synthesis and reactivity dienamines, see: a) P. W. Hickmott, Tetrahedron 1984, 40, 2989-3051; b) O. Cervinka, in: The Chemistry of Enamines, Part 1, (Ed.: Z. Rappoport), Wiley, New York, 1994, chap. 9, p. 467.
13. S. Hünig, H. Kahanek, 1957, Chem. Ber. 90, 238.
14. a) A. R. Katritzky, Q-H. Long, P. Lue, Tetrahedron Lett. 1991, 32, 3597-3600;
15. b) G. Erker, M. Riedel, S. Koch, T. Jödicke, E-U. Würthwein, J. Org. Chem. 1995, 60, 5284-5290;
16. c) S. A. Kozmin, J. M. Janey, V. H. Rawal, J. Org. Chem. 1999, 64, 3039-3052;
17. d) H. McAlonan, J. P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P. K. S. Sarma, P. J. Stevenson, N. Thompson, J. Chem. Soc. Perkin Trans. 1 2002, 69-79.
18. a) J. Barluenga, F. Aznar, M. A. Fernández, C. Valdés Chem. Commun. 2002, 2362-2363;
19. b) J. Barluenga, M. A. Fernández, F. Aznar, C. Valdés Chem. Eur. J., 2004, 10, 494-507;
20. c) A. Y. Lebedev, V. V. Izmer, D. N. Kazyul'kin, I. Beletskaya, A. Z, Voskoboynikov, Org. Lett. 2002, 4, 623-626;
21. d) M. C. Willis, G. N. Brace, Tetrahedron Lett. 2002, 43, 9085-9088.
22. For reviews on the palladium-catalyzed aryl amination, see: a) J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818; b) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860; c) J. F. Hartwig, in: Modern Amination Methods. (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; d) A. R Muci, S. L. Buchwald, Topics in Current Chemistry, 2002, 219, 133-209.
23. For reviews on the palladium-catalyzed aryl amination, see: a) J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818; b) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860; c) J. F. Hartwig, in: Modern Amination Methods. (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; d) A. R Muci, S. L. Buchwald, Topics in Current Chemistry, 2002, 219, 133-209.
24. For reviews on the palladium-catalyzed aryl amination, see: a) J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818; b) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860; c) J. F. Hartwig, in: Modern Amination Methods. (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; d) A. R Muci, S. L. Buchwald, Topics in Current Chemistry, 2002, 219, 133-209.
25. For reviews on the palladium-catalyzed aryl amination, see: a) J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818; b) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860; c) J. F. Hartwig, in: Modern Amination Methods. (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; d) A. R Muci, S. L. Buchwald, Topics in Current Chemistry, 2002, 219, 133-209.
26. For copper-catalyzed amidations of alkenyl bromides and iodides, see: a) L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett. 2003, 5, 3667-3669; b) C. Han, R. Shen, S. Su, J. A. Porco, Jr., Org. Lett. 2004, 6, 27-30; c) R. S. Coleman, P-H. Liu, Org. Lett. 2004, 6, 577-580.
27. For copper-catalyzed amidations of alkenyl bromides and iodides, see: a) L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett. 2003, 5, 3667-3669; b) C. Han, R. Shen, S. Su, J. A. Porco, Jr., Org. Lett. 2004, 6, 27-30; c) R. S. Coleman, P-H. Liu, Org. Lett. 2004, 6, 577-580.
28. For copper-catalyzed amidations of alkenyl bromides and iodides, see: a) L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett. 2003, 5, 3667-3669; b) C. Han, R. Shen, S. Su, J. A. Porco, Jr., Org. Lett. 2004, 6, 27-30; c) R. S. Coleman, P-H. Liu, Org. Lett. 2004, 6, 577-580.
29. J. Barluenga, M. A. Fernández, F. Aznar, C. Valdés, Chem. Commun. 2004, 1400-1401.
30. The synthesis of 1a has been previously described: M. Oshi, K. Shirakawa, Chem. Commun. 2002, 2146-2147; however, we have found that it can be conveniently synthesized by a hydrozirconation-bromination sequence (see Supplementary Information for experimental details).
31. D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
32. X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653.
33. S. Abbas, C. J. Hayes, S. Worden, Tetrahedron Lett. 2000, 41, 3215-3219.
34. The enamine 3i undergoes complete isomerization into the (E, E) isomer upon heating neat at 60°C for 1 h.
35. M. Qian, Z. Huang, and E. Negishi, Org. Lett. 2004, 6, 1531-1534.
36. a) V. Ratovelomanana, G. Linstrumelle, Tetrahedron Lett. 1984, 25, 6001-6004;
37. b) X. Chen, J. G. Millar, Synthesis 2000, 113-118.