The Directed ortho Metalation - Cross-coupling symbiosis in heteroaromatic synthesis

Journal of Heterocyclic Chemistry

Volumn 36, Issue 6, 1999, Pages 1453-1468

  Green, Laine ^a   Chauder, Brian ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; HETEROCYCLIC COMPOUND;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033395249     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360608     Document Type: Conference Paper

References (53)

1. V. Snieckus, Chem. Rev., 90, 879 (1990).
2. N. Ple, A. Turck, E. Fiquet and G. Queguiner, J. Heterocyclic Chem., 28, 283 (1991).
3. S. O. de Silva, J. N. Reed, R. J. Billedeau, X. Wang, D. J. Norris and V. Snieckus, Tetrahedron, 48, 4863 (1992).
4. M. P. Sibi and V. Snieckus, J. Org. Chem., 48, 1935 (1983).
5. S. Sengupta and V. Snieckus, Tetrahedron Letters, 31, 4267 (1990).
6. L. A. Carpino, H. Chao, S. Ghassemi, E. M. E. Mansour, C. Riemer, R. Warrass, D. Sadat-Aalaee, G. A. Truran, H. Imazumi, A. El-Faham, D. Ionescu, M. Ismail, T. L. Kowaleski, C. H. Han, H. Wenschuh, M. Beyermann, M. Bienert, H. Shroff, F. Albericio, S. A. Triolo, N. A. Sole and S. A. Kates, J. Org. Chem., 60, 7718 (1995).
7. C. Metallinos, S. Nerdinger and V. Snieckus, Organic Letters, 1, 1183 (1999).
8. M. Trost, D. L. Van Vranken, Chem. Rev., 96, 395 (1996);
9. [b] M. Shibasaki, C. D. J. Boden and A. Kojima, Tertahedron, 53, 7371 (1997);
10. [c] K. Kitayama, Y. Uozumi and T. Hayashi, Tetrahedron: Assymetry, 4, 2419 (1993);
11. [d] T. Ohkuma, H. Ooka, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 117, 10417 (1995).
12. M. Gray, B. J. Chapell, J. Felding, N. J. Taylor and V. Snieckus, Synlett, 422 (1998).
13. B. Chapell and V. Snieckus, unpublished results.
14. A. Godard, J. C. Rovera, F. Marsais, N. Ple, G. Queguiner, Tetrahedron, 48, 4123 (1992);
15. [b] F. Trecourt, M. Mallet, O. Mongin, B. Gervais and G. Queguiner, Tetrahedron, 49, 8373 (1993) and references cited therein.
16. J.-m. Fu and V. Snieckus, Tetrahedron Letters, 31, 1665 (1990).
17. S. Sengupta, M. Leite, D. S. Raslan, C. Quesnelle and V. Snieckus, J. Org. Chem., 57, 4066 (1992).
18. F. Beaulieu, Ph.D. Thesis, University of Waterloo (1994);
19. [b] K. Puumala, M.Sc. Thesis, University of Waterloo (1997).
20. S. Chamoin, S. Houldsworth, C. G. Kruse, W. I. Bakker and V. Snieckus, Tetrahedron Letters, 39, 4179 (1998).
21. E. J. Griffen, D. G Roe and V. Snieckus, J. Org. Chem., 60, 1484 (1995).
22. D. Roe and V. Snieckus, unpublished results.
23. A. C. Kinsman and V. Snieckus, Tetrahedron Letters, 40, 2453 (1998).
24. C. Quesnelle, W. Familoni and V. Snieckus, Synlett, 349 (1994);
25. [b] C. Quesnelle, Ph.D. Thesis, University of Waterloo (1996).
26. P. Beak and A. I. Meyers, Acc. Chem. Res., 6, 356 (1986).
27. G. W. Klumpp, Rec. Trav. Chim. Pays-Bas, 105, 1 (1986).
28. J.-m. Fu, B.-p. Zhao, M. J. Sharp and V. Snieckus, J. Org. Chem., 56, 1683 (1991).
29. W. Wang and V. Snieckus, J. Org. Chem., 57, 424 (1992).
30. B. I. Alo, A. Kandil, P. A. Patil, M. J. Sharp, M. A. Siddiqui, P. D. Josephy and V. Snieckus, J. Org. Chem., 56, 3763 (1991);
31. [b] A. Coelho, C. James and V. Snieckus, unpublished results.
32. C. A. James and V. Snieckus, Tetrahedron Letters, 38, 8149 (1997);
33. [b] C. A. James, Ph.D. Thesis, University of Waterloo (1992).
34. S. L. MacNeil, M. Gray, L. E. Briggs, J. J. Li and V. Snieckus, Synlett, 419 (1998);
35. [b] J. Bower, O. B. Familoni, I. Ionica and V. Snieckus, Synlett, 1081 (1997);
36. [c] F. Beaulieu and V. Snieckus, J. Org. Chem., 59, 6508 (1994);
37. [d] M. Gray, B. J. Chapell, N. J. Taylor and V. Snieckus, Angew. Chem., Int. Ed. Engl., 35, 1558 (1996).
38. S. L. MacNeil, B. Wilson and V. Snieckus, unpublished results.
39. J.-F. Marcoux, S. Doye and S. L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); For reviews on new C-N and C-O bond forming cross-coupling reactions, see B. H. Yang and S. L. Buchwald, J. Organomet. Chem., 576, 125 (1999); J. P Wolfe, S. Wagaw, J.-F. Marcoux and S. L. Buchwald, Acc. Chem. Res., 31, 805 (1998); J. F. Hartwig, Angew. Chem. Int. Ed. Engl., 37, 2047 (1998); J. F Hartwig, Synlett, 329 (1997).
40. J.-F. Marcoux, S. Doye and S. L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); For reviews on new C-N and C-O bond forming cross-coupling reactions, see B. H. Yang and S. L. Buchwald, J. Organomet. Chem., 576, 125 (1999); J. P Wolfe, S. Wagaw, J.-F. Marcoux and S. L. Buchwald, Acc. Chem. Res., 31, 805 (1998); J. F. Hartwig, Angew. Chem. Int. Ed. Engl., 37, 2047 (1998); J. F Hartwig, Synlett, 329 (1997).
41. J.-F. Marcoux, S. Doye and S. L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); For reviews on new C-N and C-O bond forming cross-coupling reactions, see B. H. Yang and S. L. Buchwald, J. Organomet. Chem., 576, 125 (1999); J. P Wolfe, S. Wagaw, J.-F. Marcoux and S. L. Buchwald, Acc. Chem. Res., 31, 805 (1998); J. F. Hartwig, Angew. Chem. Int. Ed. Engl., 37, 2047 (1998); J. F Hartwig, Synlett, 329 (1997).
42. J.-F. Marcoux, S. Doye and S. L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); For reviews on new C-N and C-O bond forming cross-coupling reactions, see B. H. Yang and S. L. Buchwald, J. Organomet. Chem., 576, 125 (1999); J. P Wolfe, S. Wagaw, J.-F. Marcoux and S. L. Buchwald, Acc. Chem. Res., 31, 805 (1998); J. F. Hartwig, Angew. Chem. Int. Ed. Engl., 37, 2047 (1998); J. F Hartwig, Synlett, 329 (1997).
43. J.-F. Marcoux, S. Doye and S. L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); For reviews on new C-N and C-O bond forming cross-coupling reactions, see B. H. Yang and S. L. Buchwald, J. Organomet. Chem., 576, 125 (1999); J. P Wolfe, S. Wagaw, J.-F. Marcoux and S. L. Buchwald, Acc. Chem. Res., 31, 805 (1998); J. F. Hartwig, Angew. Chem. Int. Ed. Engl., 37, 2047 (1998); J. F Hartwig, Synlett, 329 (1997).
44. A. V. Kalinin, J. F. Bower, P. Riebel and V. Snieckus, J. Org. Chem., 64, 2986 (1999).
45. F. Thiel, Angew. Chem. Int. Ed. Engl., 38, 2345 (1999).
46. K. C. Nicolaou, H. J. Mitchell, N. F. Jain, N. Winssinger, R. Hughes and T. Bando, Angew. Chem. Int. Ed. Engl., 38, 240 (1999);
47. [b] D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow and J. L. Katz, Angew. Chem. Int. Ed. Engl., 37, 2700 (1998);
48. [c] D. L. Boger, S. Miyazaki, S. H. Kim, J. H. Wu, O. Loiseleur and S. L. Castle, J. Am. Chem. Soc., 121, 3226 (1999).
49. R. H. Grubbs and S. Chang, Tetrahedron, 54, 4413 (1998);
50. [b] S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 371 (1998);
51. [c] B. A. Chauder, Synlett, 267 (1999).
52. M. Stefinovic and V. Snieckus, J. Org. Chem., 63, 2808 (1997).
53. C. Lane and V. Snieckus, unpublished results.