Regioselective Pd(0)-catalyzed Hiyama cross-coupling reactions at dihalo-substituted heterocycles

Synlett

Volumn , Issue 1, 2010, Pages 81-84

  Schweizer, Stefan A ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Catalysis; Cross coupling; Heterocycles; Palladium; Regioselectivity; Silane

Indexed keywords

BENZENE; CARBOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; METHYL 2,3 DIBROMO 5 FURANCARBOXYLATE; N OCTYLTRIFLUOROSILANE; PALLADIUM; SILANE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL PHENOMENA; CONTROLLED STUDY; CROSS COUPLING REACTION; REACTION OPTIMIZATION; REGIOSELECTIVITY;

EID: 77951696770     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218528     Document Type: Article

References (37)

1. (a) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell: Oxford, 2000.
2. (b) Gilchrist, T. L. Heterocyclic Chemistry, 3rd ed.; Longman: Harlow, 1997.
3. (c) Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles, 2nd ed.; Wiley-VCH: Weinheim, 2003.
4. (d) Li, J. J.; Gribble, G. W. Palladium In Heterocyclic Chemistry; Pergamon Press: Oxford, 2000.
5. For reviews, see: (a) Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
6. (b) Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036.
7. Bach, T.; Bartels, M. Synthesis 2003, 925.
8. (a) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507.
9. (b) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437.
10. For reviews, see: (a) Hiyama, T. in Metal-Catalyzed CrossCoupling Reactions; Diederich, F.; Stang, P. J., Eds.; WileyVCH: Weinheim, 1998, 421-453.
11. (b) Denmark, S. E.; Sweis, R. F. in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Vol.1; de Meijere, A.; Diederich, F., Eds.; WileyVCH: Weinheim, 2004, 163-216.
12. (a) Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem. Int. Ed. 2007, 46, 3556.
13. (b) Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302.
14. (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
15. (b) Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495.
16. (c) Denmark, S. E.; Sweis, R. F. Chem, Pharm. Bull. 2002, 50, 1531.
17. (d) Denmark, S. E.; Ober, M. H. Adv. Synth. Catal. 2004, 346, 1703.
18. (e) Denmark, S. E.; Regens, C. S. Acc. Chem. Res. 2008, 41, 1486.
19. (f) Denmark, S. E.; Werner, N. S. J. Am. Chem. Soc. 2008, 130, 16382.
20. (g) Denmark, S. E.; Smith, R. C.; Chang, W.-T. T.; Muhui, J. M. J. Am. Chem. Soc. 2009, 131, 3104.
21. Bury, P.; Hareau, G.; Kocieński, P.; Dhanak, D. Tetrahedron 1994, 50, 8793.
22. Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1990, 31, 2719.
23. 3 as the catalyst. Almost no conversion was achieved with the given activating reagents, while anhydrous CsF delivered a significant conversion after 18 h (26% 4a, 34% 5).
24. (a) Bach, T.; Krüger, L. Tetrahedron Lett. 1998, 39, 1729.
25. (b) Bach, T.; Krüger, L. Synlett 1998, 1185.
26. (c) Bach, T.; Krüger, L. Eur. J. Org. Chem. 1999, 2045.
27. 3), 1,2-bis(diphenylphosphino)ethane (dppe), 1,2-bis(di-2- furylphosphino)ethane (dfpe), and 1,4bis(diphenylphosphino)butane (dppb).
28. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
29. (b) Amatore, C.; Jutand, A.; Meyer, G.; Atmani, H.; Khalil, F.; Chahdi, F. O. Organometallics 1998, 17, 2958.
30. (c) For a review, see: Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
31. 3: 316.0674; found: 316.0673.
32. A guide for predicting regioselectivity in cross-coupling reactions has been suggested, see: Handy, S. T.; Zhang, Y. Chem. Commun. 2006, 299.
33. For Suzuki cross-coupling of 2,4-dibromopyridine, see: (a) Sicre, C.; Alonso-Gómez, J.-L.; Cid, M. M. Tetrahedron 2006, 62, 11063.
34. (b) Voisin-Chiret, A. S.; Bouillon, A.; Burzicki, G.; Célant, M.; Legay, R.; El-Kashef, H.; Rault, S. Tetrahedron 2009, 65, 607.
35. For Pd-catalyzed amination of 2, 4-dibromopyridine, see: Denhart, D. J.; Purandare, A. V.; Catt, J. D.; King, H. D.; Gao, A.; Deskus, J. A.; Poss, M. A.; Stark, A. D.; Torrente, J. R.; Johnson, G.; Mattson, R. J. Bioorg. Med. Chem. Lett. 2004, 14, 4249.
36. (a) Damrauer, R.; Danahey, S. E. Organometallics 1986, 5, 1490.
37. (b) Schraml, J.; Chvalovsk, V.; Mägi, M.; Lippmaa, E. J. Organomet. Chem. 1973, 51, C5.