Synthesis of N-aryl pyridin-2-ones via ligand coupling reactions using pentavalent organobismuth reagents

Chemistry Letters

Volumn 34, Issue 11, 2005, Pages 1496-1497

  Ikegai, Kazuhiro ^a,b   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544443298     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1496     Document Type: Article

References (33)

1. a) C. S. Li and D. D. Dixon, Tetrahedron Lett., 45, 4257 (2004).
2. b) W. Wawzonek and T. V. Truong, J. Heterocycl. Chem., 25, 381 (1988), and references therein.
3. For reviews on copper-catalyzed Ullman reactions, see: a) J. Lindley, Tetrahedron, 40, 1433 (1984).
4. b) S. V. Ley and A. W. Thomas, Angew. Chem., Int. Ed., 42, 5400 (2003).
5. a) W. W. K. R. Mederski, M. Lefort, M. Germann, and D. Kux, Tetrahedron, 55, 12757 (1999).
6. b) P. Y. S. Lam, G. Vincent, C. G. Clark, S. Deudon, and P. K. Jadhav, Tetrahedron Lett., 42, 3415 (2001).
7. c) B. Renger, Synthesis, 1985, 856.
8. d) M. Sugahara and T. Ukita, Chem. Pharm. Bull., 45, 719 (1997).
9. For reviews on organobismuth chemistry, see: a) R. A. Abramovitch, D. H. R. Barton, and J.-P. Finet, Tetrahedron, 44, 3039 (1988).
10. b) J.-P. Finet, Chem. Rev., 89, 1487 (1989).
11. c) Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 69, 2673 (1996).
12. d) H. Suzuki, T. Ikegaimi, Y. Matano, Synthesis, 1997, 249.
13. e) N. Komatsu, in "Organobismuth Chemistry," ed. by H. Suzuki and Y. Matano, Elsevier, New York (2001), Chap. 5, p 371.
14. f) G. I. Elliott and J. P. Konopelski, Tetrahedron, 57, 5683 (2001).
15. a) D. H. R. Barton, J.-P. Finet, W. B. Motherwell, and C. Pichon, J. Chem. Soc., Perkin Trans. 1, 1987, 251.
16. b) S. David and A. Thieffry, J. Org. Chem., 48, 441 (1983).
17. a) D. H. R. Barton, N. Y. Bhatnagar, J.-C. Blazejewski, B. Charpiot, J.-P. Finet, D. J. Lester, W. B. Motherwell, M. T. B. Papoula, and S. P. Stanforth, J. Chem. Soc., Perkin Trans. 1, 1985, 2657.
18. b) D. H. R. Barton, N. Y. Bhatnagar, J.-P. Finet, J. Khamsl, W. B. Motherwell, and S. P. Stanforth, Tetrahedron, 43, 323 (1987).
19. a) D. H. R. Barton, J.-C. Blazejewski, B. Charpiot, J.-P. Finet, W. B. Motherwell, M. T. B. Papoula, and S. P. Stanforth, J. Chem. Soc., Perkin Trans. 1, 1985, 2667.
20. b) R. S. Fornicola, E. Oblinger, and J. Montgomery, J. Org. Chem., 63, 3528 (1998).
21. c) K. C. Santhosh and K. K. Balasubramanian, J. Chem. Soc., Chem. Commun., 1992, 224.
22. a) T. Ooi, R. Goto, and K. Maruoka, J. Am. Chem. Soc., 125, 10494 (2003).
23. b) T. Arnauld and D. H. R. Barton, J. Org. Chem., 64, 6915 (1999).
24. P. K. Koech and M. J. Krische, J. Am. Chem. Soc., 126, 5350 (2004).
25. a) T. Arnauld, D. H. R. Barton, and E. Doris, Tetrahedron, 53, 4137 (1997).
26. b) D. H. R. Barton, J.-P. Finet, and J. Khamsi, Tetrahedron Lett., 30, 937 (1989).
27. c) D. H. R. Barton, J.-P. Finet, and J. Khamsi, Tetrahedron Lett., 27, 3615 (1986).
28. A few examples of N-phenylation with organobismuth compounds in the absence of copper catalysts were reported. a) D. H. R. Barton, J.-P. Finet, and C. Pichon, J. Chem. Soc., Chem. Commun., 1986, 65.
29. b) M. S. Akhtar, W. J. Brouillette, and D. V. Waterhous, J. Org. Chem., 55, 5222 (1990). See also Ref. 5a.
30. 2 were mixed at room temperature, the product 1a was formed only in 40% yield.
31. The use of sodium hydride or 1,1,3,3-tertramethylguanidine was less effective compared with that of t-BuOK in N-o-tolylation of pyridin-2-one (75 or 69% yield, respectively).
32. Unfortunately, our attempt to isolate bismuth(III)-byproducts was unsuccessful owing to their labilities, while small amounts of triarylbismuthines were detected together with N-arylated products.
33. Y. Matano, S. A. Begum, T. Miyamatsu, and H. Suzuki, Organometallics, 17, 4332 (1998).