PdX2/CuX2-catalyzed annulation of 2-ethynylbenzeneamines: Selective synthesis of 2-substituted 3-halo-1H-indoles

Synthesis

Volumn , Issue 12, 2007, Pages 1841-1847

  Tang, Shi ^a,b   Xie, Ye Xiang ^a   Li, Jin Heng ^a   Wang, Nai Xing ^b  

^a HUNAN NORMAL UNIVERSITY   (China)

^b TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

2 ethynylbenzeneamine; 2 substituted 3 halo 1H indoles; Annulation; Copper(II) halide; Palladium(II) halide

Indexed keywords

CATALYZED ANNULATION; EFFECTIVE PROTOCOL;

CATALYSIS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AMINES;

2 ETHYNYLBENZENEAMINE; 3 HALO 1H INDOLE; BENZYLAMINE DERIVATIVE; COPPER COMPLEX; INDOLE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE;

EID: 34347382389     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983717     Document Type: Article

References (59)

1. For recent reviews, see: (a) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
2. (b) Gribble, G. W. Chem. Soc. Rev. 1999, 28, 335.
3. (c) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon: Amsterdam, 2000.
4. (d) Gribble, G. W. Environ. Sci. Pollut. Res. 2000, 7, 37.
5. (e) Lu, X. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2; Negishi, E., Ed.; Wiley-Interscience: New York, 2002, 2267-2288.
6. (f) Knölker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
7. (g) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
8. (h) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
9. (i) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
10. (j) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
11. For selected papers, see: (a) Carter, G. T.; Rinehart, K. L. Jr.; Li, H. L.; Connor, S. L. K. L. Tetrahedron Lett. 1978, 19, 4479.
12. (b) Tarzia, G.; Diamantini, G.; Giacomo, B. D.; Spadoni, G. J. Med. Chem. 1997, 40, 2003.
13. (c) He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.
14. (d) Kanekiyo, N.; Kuwada, T.; Choshi, T.; Nobuhiro, J.; Hibino, S. J. Org. Chem. 2001, 66, 8793.
15. (e) Zhang, H.; Larock, R. C. Org. Lett. 2001, 3, 3083.
16. (f) Zhang, H.; Larock, R. C. J. Org. Chem. 2002, 67, 9318.
17. (g) Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861.
18. (h) Rawat, M.; Wulff, W. D. Org. Lett. 2004, 6, 329.
19. (i) Nicolaou, K. C.; Snyder, S. A.; Huang, X. H.; Simonsen, K. B.; Koumbis, A. E.; Bigot, A. J. Am. Chem. Soc. 2004, 126, 10162.
20. (j) Frohner, W.; Monse, B.; Braxmeier, T. M.; Casiraghi, L.; Sahagun, H.; Seneci, P. Org. Lett. 2005, 7, 4573.
21. (k) Ludwig, J.; Bovens, S.; Brauch, C.; Elfringhoff, A. S.; Lehr, M. J. Med. Chem. 2006, 49, 2611.
22. For representative papers on the synthesis 3-haloindole mediated by N-halosuccinimides, see: (a) Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1982, 47, 757.
23. (b) Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1983, 48, 2690.
24. (c) Mistry, A. G.; Smith, K.; Bye, M. R. Tetrahedron Lett. 1986, 27, 1051.
25. (d) Kobayashi, Y.; Fujimoto, T.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 6501.
26. (e) Katayama, S.; Ae, N.; Nagata, R. J. Org. Chem. 2001, 66, 3474.
27. (f) Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.
28. (a) Bocchi, V.; Palla, G. Synthesis 1982, 1096.
29. (b) Martin, P. Tetrahedron Lett. 1987, 28, 1645.
30. (c) Martin, P. Helv. Chim. Acta 1988, 71, 344.
31. (d) Timms, G. H.; Tupper, D. E.; Morgan, S. E. J. Chem. Soc., Perkin Trans. 1 1989, 817.
32. (e) Billimoria, A. D.; Cava, M. P. J. Org. Chem. 1994, 59, 6777.
33. (f) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879.
34. (a) Akinori, K.; Tatsuya, N. Synthesis 1980, 365.
35. (b) Tarzia, G.; Diamantini, G.; Giacomo, B. Di.; Spadoni, G. J. Med. Chem. 2000, 43, 2449.
36. For selected papers on the other transformations for the synthesis of 3-haloindoles, see: (a) Bergman, J.; Carlsson, R.; Sjoberg, B. J. Heterocycl. Chem. 1977, 14, 1123.
37. (b) Kubo, A.; Uchino, K. Heterocycles 1981, 16, 1441.
38. (c) Gribble, G. W.; Allison, B. D.; Conway, S. C.; Saulnier, M. G. Org. Prep. Proced. Int. 1992, 24, 649.
39. (d) Witulsk, B.; Buschmann, N.; Bergsträßer, U. Tetrahedron 2000, 56, 8473.
40. (e) Balogh-Hergovich, É.; Speier, G. J. Chem. Soc., Perkin Trans. 1 1986, 2305.
41. (f) Tang, S.; Li, J.-H.; Xie, Y.-X.; Wang, N.-X. Synthesis 2007, 1535.
42. (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem. Int. Ed. 2003, 42, 2406.
43. (b) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
44. (c) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
45. (d) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62.
46. Liang, Y.; Tang, S.; Zhang, X.-D.; Mao, L.-Q.; Xie, Y.-X.; Li, J.-H. Org. Lett. 2006, 8, 3017.
47. 2 affects the reaction. This is may be because the concentration of the halide ions can stabilize intermediate 6 in Scheme 2. However, more halide ions result in some side-reactions. For the effect of the halide ion on the halopalladation reaction in detail, see reference 1d and: Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120.
48. It has been reported that Cu(II) as an oxidant could cleave the C-Pd σ-bond, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393.
49. (b) Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
50. (c) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
51. (d) Li, J.-H.; Jiang, H.-F.; Feng, A.-Q.; Jia, L.-Q. J. Org. Chem. 1999, 64, 5984.
52. (e) Li, J.-H.; Jiang, H.-F.; Chen, M.-C. J. Org. Chem. 2001, 66, 3627.
53. (f) Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org. Chem. 2004, 69, 8125.
54. (g) Li, J.-H.; Tang, S.; Xie, Y.-X. J. Org. Chem. 2005, 70, 477.
55. For recent representative papers on protonolysis of the Pd complex to regenerate the active Pd(II) species by HCl, see: (a) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290.
56. (b) Yang, D.; Li, J.-H.; Gao, Q.; Yan, Y.-L. Org. Lett. 2003, 5, 2869.
57. (c) Han, X.; Wang, X.; Pei, T.; Widenhoefer, R. A. Chem. Eur. J. 2004, 10, 6333; and references cited therein.
58. (d) Li, J.-H.; Zhu, Q.-M.; Liang, Y.; Yang, D. J. Org. Chem. 2005, 70, 5347.
59. Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126.