Synthesis of 2,2-Bipyridines via Suzuki-Miyaura Cross-Coupling

Synthesis

Volumn , Issue 1, 2010, Pages 85-90

  Gütz, Christoph ^a   Lützen, Arne ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

2 pyridylboronic acid esters; Bipyridines; Cross coupling reactions; Palladium; Suzuki Miyaura reaction

Indexed keywords

ACID ESTER; BIPYRIDINES; CROSS COUPLING REACTIONS; FUNCTIONALIZED; SUZUKI-MIYAURA CROSS-COUPLING; SUZUKI-MIYAURA CROSS-COUPLING REACTION; SUZUKI-MIYAURA REACTION;

ACIDS; ESTERIFICATION; ESTERS; PALLADIUM; SYNTHESIS (CHEMICAL);

COMPLEXATION;

2,2' BIPYRIDINE DERIVATIVE; BORON DERIVATIVE; BORONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 75749115600     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217082     Document Type: Article

References (40)

1. Mongin F, Trecourt F, Gervais B, Mongin O, Quguiner G, J. Org. Chem. 2002 67 3272
2. Sammakia T, Stangeland E L., Whitcomb M C., In Strategies and Tactics in Organic Synthesis Vol. 6
3. Harmata M, Elsevier New York 2005 415
4. and references cited therein, Trecourt F, Gervais B, Mongin O, LeGal C, Mongin F, Quguiner G, J. Org. Chem. 1998 63 2892
5. Du W, Tetrahedron 2003 59 8649
6. Bringmann G, Reichert Y, Kane V V., Tetrahedron 2004 60 3539
7. Smith A P., Fraser C L., In Comprehensive Coordination Chemistry II Vol. 1, McCleverty J A., Meyer T J., Elsevier Oxford 2004 1
8. Kaes C, Katz A, Hosseini M W., Chem. Rev. 2000 100 3553, Schalley C A., Ltzen A, Albrecht M, Chem. Eur. J. 2004 10 1072, Hannon M J., Childs L J., Supramol. Chem. 2006 16 7
9. Photochemistry and Photophysics of Coordination Compounds I, In Topics in Current Chemistry Vol. 280
10. Balzani V, Campagna S, Springer Berlin 2007 Photochemistry and Photophysics of Coordination Compounds II, In Topics in Current Chemistry Vol. 281
11. Balzani V, Campagna S, Springer Berlin 2007
12. Recent review with focus on chiral 2,2′ -bipyridines:, Malkov A V., Koovs P, Curr. Org. Chem. 2003 7 1737; and references cited therein
13. Kwong H.-L, Yeung H.-L, Yeung C.-T, Lee W.-S, Lee C.-S, Wong W.-L, Coord. Chem. Rev. 2007 251 2188
14. Newkome G R., Patri A K., Holder E, Schubert U S., Eur. J. Org. Chem. 2004 235, Hapke M, Brandt L, Ltzen A, Chem. Soc. Rev. 2008 37 2782
15. Krhnke F, Synthesis 1976 1
16. Special Issue on 30 Years of the Cross-Coupling Reaction, In J. Organomet. Chem. 2002 653 1-303
17. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 2004.
18. Cross-Coupling Reactions, In Topics in Current Chemistry, Vol. 219; Miyaura, N., Ed.; Springer: Berlin, 2002.
19. Deshayes K, Broene R D., Chao I, Knobler C B., Diederich F, J. Org. Chem. 1991 56 6787
20. Fernando S R. L., Maharoof U S. M., Deshayes K D., Kinstle T H., Ogawa M Y., J. Am. Chem. Soc. 1996 118 5783
21. Miyaura N, Advances in Metal-Organic Chemistry 6, Liebeskind L S., JAI Press London 1988 187-243
22. Hodgson P B., Salingue F H., Tetrahedron Lett. 2004 45 685
23. Bouillon A, Lancelot J.-C, deOliveiraSantos J S., Collot V, Bovy P R., Rault S, Tetrahedron 2003 59 10043
24. Billingsley K L., Buchwald S L., Angew. Chem. Int. Ed. 2008 47 4695; Angew. Chem. 2009, 120, 4773
25. Knapp D M., Gillis E P., Burke M D., J. Am. Chem. Soc. 2009 131 6961
26. Deng J Z., Paone D V., Ginetti A T., Kurihara H, Dreher S D., Weissman S A., Stauffer S R., Burgey C S., Org. Lett. 2009 11 345
27. Yang D X., Colletti S L., Wu K, Song M, Li G Y., Shen H C., Org. Lett. 2009 11 381
28. For a recent study that contains the synthesis of three 2,2-bipyridines starting from Hodgsons compounds, see:, Jones N A., Antoon J W., Bowie A L. Jr., Borak J B., Stevens E P., J. Heterocycl. Chem. 2007 44 363
29. Pierrat P, Gros P, Fort Y, Org. Lett. 2005 7 697
30. Kiehne U, Bunzen J, Staats H, Ltzen A, Synthesis 2007 1061
31. Fang Y.-Q, Hanan G S., Synlett 2003 852
32. Potts K T., Winslow P A., J. Org. Chem. 1985 40 5405
33. Pojer P M., Summers L A., J. Heterocycl. Chem. 1974 11 303
34. Panette C A., Kumpaty H J., Jeimer N E., Leavy M C., Hussey C L., J. Org. Chem. 1999 64 1015
35. Flechter N C., Niveuwenhuyzen M, Rainey S, J.Chem. Soc., Dalton Trans. 2001 2641
36. Zhang B, Breslow R, J. Am. Chem. Soc. 1997 119 1676
37. Heirtzler F R., Neuburger M, Zehnder M, Constable E C., Liebigs Ann. Chem. 1997 297
38. Ltzen A, Hapke M, Staats H, Bunzen J, Eur. J. Org. Chem. 2003 3948
39. Schein C H., Chen D, Gilbertson S R., Estrella-Jimenez M, Gao J, Walter M A., Peterson J W., PCT Int. Appl. WO 2009038842 2009
40. Chem. Abstr. 2009, 150, 351761