Site-selective Suzuki-Miyaura reactions of 2,3,5-tribromo-N-methylpyrrole

Tetrahedron Letters

Volumn 52, Issue 29, 2011, Pages 3732-3735

  Toguem, Serge Mithérand Tengho ^a   Fatunsin, Olumide ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Catalysis; Palladium; Pyrroles; Site selectivity; Suzuki Miyaura reaction

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ELECTRON; HALOGENATION; ONE POT SYNTHESIS; SUZUKI MIYAURA REACTION; SUZUKI REACTION;

EID: 79959223931     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.044     Document Type: Article

References (39)

1. (a) Jones, R. A.; Bean, G. P. The chemistry of pyrrole; Academic Press: London, 1977;
2. (b)Pyrroles Part 1; Jones, R. A., Ed.; Wiley-Interscience: New York, 1990;
3. (c) Jefford, C. W. Curr. Org. Chem. 2000, 4, 205;
4. (d) Banwell, M. G.; Beck, D. A. S.; Stanislawski, P. C.; Sydnes, M. O.; Taylor, R. M. Curr. Org. Chem. 2005, 9, 1589;
5. (e) Baumann, K. L.; Butler, D. E.; Deering, C. F.; Mennen, K. E.; Millar, A.; Nanninga, T. N.; Palmer, C. W.; Roth, B. D. Tetrahedron Lett. 1992, 33, 2283;
6. (f) Sternberg, E. D.; Dolphin, D.; Brückner, C. Tetrahedron 1998, 54, 4151;
7. (g) Sato, A.; McNulty, L.; Cox, K.; Kim, S.; Scott, A.; Daniell, K.; Summerville, K.; Price, C.; Hudson, S.; Kiakos, K.; Hartley, J. A.; Asao, T.; Lee, M. J. Med. Chem. 2005, 48, 3903.
8. (a) Bailly, C. Curr. Med. Chem. Anti-Cancer Agents 2004, 4, 363;
9. (b) Handy, S. T.; Zhang, Y. Org. Prep. Proceed. Int. 2005, 37, 411;
10. (c) Pla, D.; Marchal, A.; Olsen, C. A.; Albericio, F.; Álvarez, M. J. Org. Chem. 2005, 70, 8231.
11. Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry Tetrahedron Organic Chemistry Series; Elsevier Science Ltd.: Oxford, 2000; vol. 20, Chapter 2.
12. (a) Cox, M.; Lehninger, A. L.; Nelson, D. R. Lehninger principles of biochemistry; Worth Publishers: New York, 2000;
13. (b) De Leon, C. Y.; Ganem, B. Tetrahedron 1997, 53, 7731;
14. (c) Danso-Danquah, R. E.; Scott, A. I. Tetrahedron 1993, 49, 8195.
15. van Pée, K.-H.; Ligon, J. M. Nat. Prod. Rep. 2000, 17, 157.
16. For reviews of cross-coupling reactions of polyhalogenated heterocycles, see: (a) Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245;
17. (b) Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 3283;
18. (c) Wang, R.; Manabe, K. Synthesis 2009, 1405.
19. For work from our laboratories, see: (a) Dang, T. T.; Dang, T. T.; Ahmad, R.; Reinke, H.; Langer, P. Tetrahedron Lett. 2008, 49, 1698;
20. (b) Dang, T. T.; Villinger, A.; Langer, P. Adv. Synth. Catal. 2008, 350, 2109;
21. (c) Hussain, M.; Nguyen, T. H.; Langer, P. Tetrahedron Lett. 2009, 50, 3929;
22. (d) Tengho Toguem, S.-M.; Hussain, M.; Malik, I.; Villinger, A.; Langer, P. Tetrahedron Lett. 2009, 50, 4962;
23. (e) Hussain, M.; Malik, I.; Langer, P. Synlett 2009, 2691;
24. (f) Dang, T. T.; Dang, T. T.; Rasool, N.; Villinger, A.; Langer, P. Adv. Synth. Catal. 2009, 351, 1595;
25. (g) Ullah, I.; Khera, R. A.; Hussain, M.; Langer, P. Tetrahedron Lett. 2009, 50, 4651;
26. (h) Nawaz, M.; Farooq, M. I.; Obaid-Ur-Rahman, A.; Khera, R. A.; Villinger, A.; Langer, P. Synlett 2010, 150;
27. (i) Toguem, S.-M. T.; Villinger, A.; Langer, P. Synlett 2009, 3311;
28. (j) Toguem, S.-M. T.; Villinger, A.; Langer, P. Synlett 2010, 909.
29. Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036.
30. Schröter, S.; Bach, T. Synlett 2005, 1957.
31. (a) Handy, S. T.; Sabatini, J. J. Org. Lett. 2006, 8, 1537;
32. (b) Handy, S. T.; Zhang, Y. N. Synthesis 2006, 3883.
33. Beaumard, F.; Dauban, P.; Dodd, R. H. Org. Lett. 2009, 11, 1801.
34. Gilow, H. M.; Burton, D. E. J. Org. Chem. 1981, 46, 2221.
35. 2: 342.93888; found: 342.939847.
36. CCDC-824509 (3a) and CCDC-824510 (6a) contain all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; Fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk.
37. 22NBr: 367.09301; found: 367.09300.
38. 3N: 399.18290; found: 399.18262.
39. 1H NMR chemical shifts of the non-halogenated parent compound, see: Handy, S. T.; Zhang, Y. Chem. Commun. 2006, 299.