Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions

Chemical Communications

Volumn , Issue 8, 2005, Pages 973-986

  Dehli, Juan R ^a   Legros, Julien ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; COPPER COMPLEX; ENAMINE; ETHER DERIVATIVE; NATURAL PRODUCT; PALLADIUM; VINYL DERIVATIVE;

ARYLATION; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REVIEW; SYNTHESIS;

EID: 14944348646     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415954c     Document Type: Review

References (80)

1. (a) A. De Meijere and F. Diederich, Metal-catalyzed Cross-coupling Reactions, Wiley-VCH, New York, 2nd edn., 2004;
2. (b) Modern Amination Methods, ed. A. Ricci, Wiley-VCH, Weinheim, 2000.
3. (a) A. R. Muci and S. L. Buchwald, Top. Curr. Chem., 2002, 219, 131;
4. (b) J. F. Hartwig in Handbook of Organopalladium Chemistry for Organic Synthesis, ed. E. Negishi, Wiley, New York, 2002, p. 1051.
5. Y. Sugie, K. A. Dekker, H. Hirai, T. Ichiba, M. Ishiguro, Y. Shiomi, A. Sugiura, L. Brennan, J. Duignan, L. H. Huang, J. Sutcliffe and Y. Kojima, J. Antibiot., 2001, 54, 1060.
6. For a review on the chemistry and biology of these compounds, see: L. Yet, Chem. Rev., 2003, 103, 4283.
7. Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd edn., R. L. Larock, Wiley-VCH, New York, 1999, p. 1507.
8. (a) Enamines: Synthesis, Structure and Reactions, ed A. G. Cook, Marcel Dekker, New York, 2nd edn., 1987;
9. (b) The Chemistry of Enamines, ed. Z. Rappaport, J. Wiley, Chichester, UK, 1994.
10. (a) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack and H. Trauthwein, Synlett, 2002, 1579;
11. (b) M. Beller, J. Seayad, A. Tillack and H. Jiao, Angew. Chem. Int. Ed., 2004, 43, 3368.
12. N. A. Petasis and S. P. Lu, Tetrahedron Lett., 1995, 36, 2393.
13. R. E. Kirk and D. F. Othmer, Encyclopedia of Chemical Technology, 4th edn., John Wiley and Sons, New York, 1991, vol. 1.
14. Y. Okimoto, S. Sakaguchi and Y. Ishii, J. Am. Chem. Soc., 2002, 124, 1590.
15. (a) U. K. Singh, E. R. Strieter, D. G. Blackmond and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 14104;
16. (b) L. M. Alcazar-Roman, J. F. Hartwig, A. L. Rheingold, L. M. Liable-Sands and I. A. Guzei, J. Am. Chem. Soc., 2000, 122, 4618.
17. A. Y. Lebedev, V. V. Izmer, D. N. Kazyul'kin, I. P. Beletskaya and A. Z. Voskoboynikov, Org. Lett., 2002, 4, 623.
18. J. Barluenga, M. A. Fernández, F. Aznar and C. Valdés, Chem. Commun., 2002, 2362.
19. J. Barluenga, M. A. Fernández, F. Aznar and C. Valdés, Chem. Eur. J., 2004, 10, 494.
20. A. Jutand and S. Négri, Organometallics, 2003, 22, 4229.
21. J. Barluenga, M. A. Fernández, F. Aznar and C. Valdés, Chem. Commun., 2004, 1400.
22. For reviews on synthesis and reactivities of vinyl Inflates, see: (a) K. Ritter, Synthesis, 1993, 735;
23. (b) P. J. Stang, M. Hanack and L. R. Subramanian, Synthesis, 1982, 85.
24. F. A. Hicks and M. Brookhart, Org. Lett., 2000, 2, 219.
25. M. C. Willis and G. N. Brace, Tetrahedron Lett., 2002, 43, 9085.
26. (a) Y. Kozawa and M. Mori, Tetrahedron Lett., 2002, 43, 111;
27. (b) Y. Kozawa and M. Mori, J. Org. Chem., 2003, 68, 3064.
28. D. J. Wallace, D. J. Klauber, C.-Y. Chen and R. P. Volante, Org. Lett., 2003, 5, 4749.
29. J. L. Brice, J. E. Meerdink and S. S. Stahl, Org. Lett., 2004, 6, 1845.
30. J. Barluenga, F. Aznar and C. Valdés, Angew. Chem. Int. Ed., 2004, 43, 343.
31. For recent reviews on sulfoximines and their use in asymmetric catalysis, see: (a) M. Reggelin and C. Zur, Synthesis, 2000, 1;
32. (b) M. Harmata, Chemtracts, 2003, 16, 660;
33. H. Okamura and C. Bolm, Chem. Lett., 2004, 33, 482.
34. (a) C. Bolm and J. P. Hildebrand, J. Org. Chem., 2000, 65, 169;
35. (b) G. Y. Cho, P. Rémy, J. Jannsson, C. Moessner and C. Bolm, Org. Lett., 2004, 6, 3293.
36. For representative examples, see: (a) C. Bolm and O. Simic, J. Am. Chem. Soc., 2001, 123, 3830;
37. (b) C. Bolm, M. Verrucci, O. Simic, P. G. Cozzi, G. Raabe and H. Okamura, Chem. Commun., 2003, 2826;
38. M. Langner and C. Bolm, Angew. Chem. Int. Ed., 2004, 43, 5984.
39. C. Bolm, C. P. R. Hackenberger, O. Simic, M. Verrucci, D. Müller and F. Bienewald, Synthesis, 2002, 879 and references therein.
40. J. R. Dehli and C. Bolm, J. Org. Chem., 2004, 69, 8518.
41. J. F. Hartwig, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed. E. Negishi, Wiley: New York, 2002, p. 1097.
42. (a) R. Rossi, F. Bellina and L. Mannina, Tetrahedron, 1997, 53, 1025;
43. (b) R. Rossi, F. Bellina and A. Carpita, Synlett, 1996, 356.
44. M. C. Willis, D. Taylor and A. T. Gillmore, Chem. Commun., 2003, 2222.
45. W. H. Watanabe and L. E. Conlon, J. Am. Chem. Soc., 1957, 79, 2828.
46. P. M. Weintraub and C.-H. R. King, J. Org. Chem., 1997, 62, 1560.
47. S. Handerson and M. Schlaf, Org. Lett., 2002, 4, 407.
48. M. Bosch and M. Schlaf, J. Org. Chem., 2003, 68, 5225.
49. For reviews on copper-mediated cross-couplings, see: (a) S. V. Ley and A. W. Thomas, Angew. Chem. Int. Ed., 2003, 42, 5400; Erratum: Angew. Chem. Int. Ed., 2004, 43, 1049;
50. For reviews on copper-mediated cross-couplings, see: (a) S. V. Ley and A. W. Thomas, Angew. Chem. Int. Ed., 2003, 42, 5400; Erratum: Angew. Chem. Int. Ed., 2004, 43, 1049;
51. (b) K. Kunz, U. Scholz and D. Ganzer, Synlett, 2003, 2428.
52. T. Ogawa, T. Kiji, K. Hayami and H. Suzuki, Chem. Lett., 1991, 1443.
53. R. Shen and J. Porco, Jr., Org. Lett., 2000, 2, 1333.
54. (a) G. D. Allred and L. S. Liebeskind, J. Am. Chem. Soc., 1996, 118, 2748;
55. (b) S. Zhang, D. Zhang and L. S. Liebeskind, J. Org. Chem., 1997, 62, 2312.
56. A. Fürstner, T. Dierckes, O. R. Thiel and G. Blanda, Chem. Eur. J., 2001, 7, 5286.
57. K. C. Nicolaou, D. W. Kim and R. Baati, Angew. Chem. Int. Ed., 2002, 41, 3701.
58. X. Wang and J. A. Porco, Jr., J. Am. Chem. Soc., 2003, 125, 6040.
59. (a) R. Shen, C. T. Lin and J. A. Porco, Jr., J. Am. Chem. Soc., 2002, 124, 5650;
60. (b) R. Shen, C. T. Lin, E. J. Bowman, B. J. Bowman and J. A. Porco, Jr., J. Am. Chem. Soc., 2003, 125, 7889.
61. C. Han, R. Shen, S. Su and J. A. Porco, Jr., Org. Lett., 2004, 6, 27, additions and corrections: Org. Lett., 2004, 6, 649.
62. C. Han, R. Shen, S. Su and J. A. Porco, Jr., Org. Lett., 2004, 6, 27, additions and corrections: Org. Lett., 2004, 6, 649.
63. R. S. Coleman and P.-H. Liu, Org. Lett., 2004, 6, 577.
64. (a) L. Jiang, G. E. Job, A. Klapars and S. L. Buchwald, Org. Lett., 2003, 5, 3667;
65. (b) see also: S. L. Buchwald, A. Klapars, J. C. Antilla, G. E. Job, M. Wolter, F. Y. Kwong, G. Nordmann and E. J. Hennessy, PCT Int. Appl., WO 2002085838, 2002.
66. X. Pan, Q. Cai and D. Ma, Org. Lett., 2004, 6, 1809.
67. J. B. Arterburn, M. Pannala and A. M. González, Tetrahedron Lett., 2001, 42, 1475.
68. P. Y. S. Lam, G. Vincent, D. Bonne and C. G. Clark, Tetrahedron Lett., 2003, 44, 4927.
69. W. Zhu and D. Ma, Chem. Commun., 2004, 888.
70. A. Hassner and F. W. Fowler, J. Org. Chem., 1968, 33, 2686.
71. J. R. Dehli and C. Bolm, Adv. Synth. Catal., accepted for publication.
72. The Cu-promoted arylation of sulfoximines has also been recently reported by the same group, see ref. 25(b).
73. For a review on the chemistry of ynamides, see: C. A. Zificsak, J. A. Mulder, R. P. Hsung, C. Rameshkumar and L.-L. Wei, Tetrahedron, 2001, 57, 7575.
74. M. O. Frederick, J. A. Mulder, M. R. Tracey, R. P. Hsung, J. Huang, K. C. M. Kurtz, L. Shen and C. J. Douglas, J. Am. Chem. Soc., 2003, 125, 2368.
75. Y. Zhang, R. P. Hsung, M. R. Tracey, K. C. M. Kurtz and E. L. Vera, Org. Lett., 2004, 6, 1151.
76. J. R. Dunetz and R. L. Danheiser, Org. Lett., 2003, 5, 4011.
77. (a) M. Keegstra, Tetrahedron, 1992, 48, 2681;
78. (b) for a stoichiometric version, see: G. M. Whitesides, J. S. Sadowski and J. Lilburn, J. Am. Chem. Soc., 1974, 96, 2829.
79. Z. Wan, C. D. Jones, T. M. Koenig, Y. J. Pu and D. Mitchell, Tetrahedron Lett., 2003, 44, 8257.
80. G. Nordmann and S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 4978.