Efficient suzuki-miyaura coupling reactions between lithium alkynyltrimethylborates and aryl chlorides

European Journal of Organic Chemistry

Volumn , Issue 6, 2006, Pages 1450-1454

  Torres, Gloria Hernández ^a   Choppin, Sabine ^a   Colobert, Françoise ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkynes; Aryl chlorides; Boron; Cross coupling; Palladium

Indexed keywords

EID: 33645046086     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500697     Document Type: Article

References (53)

1. a) K. Sonogashira, in: Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley-Interscience, New York, 2002; pp. 493-529;
2. b) E. Negishi, C. Xu in: Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley-Interscience, New York, 2002; pp. 531-549.
3. a) J. Tsuji, in: Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995;
4. b) F. Diederich, P. J. Stang, in: Metal-Catalysed Cross-Coupling Reactions, VCH, Weinheim, 1998;
5. c) N. Yoneda, S. Matsuoka, N. Miyaura, T. Fukuhara, A. Suzuki, Bull. Chem. Soc. Jpn. 1990, 63, 2124-2129.
6. R. R. Tykwinski, Angew. Chem. Int. Ed. 2003, 42, 1566-1568.
7. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4470;
8. b) S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630;
9. c) K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49;
10. d) J. C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, V. Ivonov, Org. Lett. 2004, 6, 3473-3476.
11. a) E. Negishi, in: Aspects of Mechanism and Organometallic Chemistry (Ed.: J. H. Brewster), Plenum Press, New York, 1978; pp. 285-317;
12. b) E. Negishi, Acc. Chem. Res. 1982, 15, 340-349;
13. c) F. Zeng, E. Negishi, Org. Lett. 2001, 3, 719-722;
14. d) L. Anastasia, E. Negishi, Org. Lett. 2001, 3, 3111-3113;
15. e) E. Negishi, M. Qian, F. Zeng, L. Anastasia, D. Babinski, Org. Lett. 2003, 5, 1597-1600.
16. a) T. Kamikawa, T. Hayashi, J. Org. Chem. 1998, 63, 8922-8925;
17. b) T. Kamikawa, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 3161-3164.
18. E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 1997, 38, 5177-5180.
19. D. Gelman, D. Tsvelikhovsky, G. A. Molander, J. Blum, J. Org. Chem. 2002, 67, 6287-6290.
20. a) A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90;
21. b) C. H. Oh, S. H. Jung, Tetrahedron Lett. 2000, 41, 8513-8516;
22. c) J. A. Soderquist, K. Matos, A. M. Rane, J. Ramos, Tetrahedron Lett. 1995, 36, 2401-2402;
23. d) J. A. Soderquist, A. M. Rane, K. Matos, J. Ramos, Tetrahedron Lett. 1995, 36, 6847-6850;
24. e) A. Fürstner, G. Seidel, Tetrahedron 1995, 51, 11165-11176;
25. f) A. Fürstner, K. Nikolakis, Liebigs Ann. 1996, 2107-2113;
26. g) A. Fürstner, A. Leitner, Synlett 2001, 2, 290-292.
27. a) V. V. Grushim, H. Alper, in: Activation of Unreactive Bonds and Organic Synthesis (Eds.: S. Murai), Springer, Berlin, 1999, pp. 193-226;
28. b) V. V. Grushim, H. Alper, Chem. Rev. 1994, 94, 1047-1062.
29. a) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176-4211;
30. b) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028;
31. c) M. R. Netherthon, G. C. Fu, Org. Lett. 2001, 3, 4295-4298.
32. a) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561;
33. b) T. E. Barder, S. L. Buchwald, Org. Lett. 2004, 6, 2649-2654.
34. a) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. L. Petersen, J. Org. Chem. 1999, 64, 6797-6803;
35. b) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
36. a) A. C. Hillier, G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69-82;
37. b) C. Yang, S. P. Nolan, Organometallics 2002, 21, 1020-1022;
38. c) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805.
39. a) D. A. Alonso, C. Nájera, M. C. Pacheco, Org. Lett. 2000, 2, 1823-1826;
40. b) D. A. Alonso, C. Nájera, C. Pachero, J. Org. Chem. 2002, 67, 5588-5594;
41. c) L. Botella, C. Nájera, J. Organomet. Chem. 2002, 663, 46-57;
42. d) C. Nájera, J. Gil-Molto, S. Karlstroem, Adv. Synth. Catal. 2004, 346, 1798-1811.
43. a) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. Int. Ed. 2000, 39, 4153-4155;
44. b) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 24, 2475-2476;
45. c) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. 2004, 1, 38-39;
46. d) S. Harkal, F. Rataboul, A. Zapf, C. Fuhrmann, T. Riermeier, A. Monsees, M. Beller, Adv. Synth. Catal. 2004, 346, 1742-1748.
47. V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, J. Organomet. Chem. 2000, 595, 186-190.
48. A.-S. Castanet, F. Colobert, T. Schlama, Org. Lett. 2000, 2, 3559-3561.
49. J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, in: Principles and applications of organotransition metal chemistry, Academic Press, New York, 1985.
50. R. A. Batey, M. Shen, A. J. Lough, Org. Lett. 2002, 4, 1411-1414.
51. A. J. Arduengo, R. Krafczyk, R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall, M. Unverzagt, Tetrahedron 1999, 55, 14523-14524.
52. Y. Ma, C. Song, W. Jiang, Q. Wu, Y. Wang, X. Liu, M. B. Andrus, Org. Lett. 2003, 5, 3317-3319.
53. E. Negishi, F. T. Luo, R. Frisbee, H. Matsushita, Heterocycles 1982, 18, 117-122.