Palladium-catalyzed cross-coupling of vinylic tellurides and potassium vinyltrifluoroborate salt: synthesis of 1,3-dienes

Tetrahedron Letters

Volumn 47, Issue 29, 2006, Pages 5075-5078

  Cella, Rodrigo ^a   Orfão, Aline T G ^a   Stefani, Hélio A ^a,b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Suzuki Miyaura; Tellurium compounds and ultrasound

Indexed keywords

ALKADIENE; BORIC ACID; PALLADIUM; POTASSIUM DERIVATIVE; SODIUM CHLORIDE; TELLURIUM DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS; ULTRASOUND;

EID: 33744995019     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.088     Document Type: Article

References (44)

1. For a review of metal-catalyzed Suzuki cross-coupling reactions, see:. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
2. Suzuki A. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim Chapter 2
3. Suzuki A. J. Organomet. Chem. 576 (1999) 147
4. Kotha S., Lahiri K., and Kashinath D. Tetrahedron 58 (2002) 9633
5. Suzuki A. Pure Appl. Chem. 57 (1985) 1749
6. Suzuki A. Pure Appl. Chem. 63 (1991) 419
7. Stanforth S.P. Tetrahedron 54 (1998) 263
8. Miyaura N. In: Libeskind L.S. (Ed). Advances in Metal-Organic Chemistry Vol. 6 (1998), Jai, London pp 187-243
9. Molander G.A., and Felix L.A. J. Org. Chem. 70 (2005) 3950
10. Molander G.A., Katona B.W., and Machrouhi F. J. Org. Chem. 67 (2002) 8416
11. Molander G.A., and Biolatto B. Org. Lett. 4 (2002) 1867
12. Molander G.A., and Biolatto B. J. Org. Chem. 68 (2003) 4302
13. Molander G.A., Yun C., Ribagorda M., and Biolatto B. J. Org. Chem. 68 (2003) 5534
14. Molander G.A., and Ribagorda M. J. Am. Chem. Soc. 125 (2003) 11148
15. Vedejs E., Chapman R.W., Fields S.C., Lin S., and Schrimpf M.R. J. Org. Chem. 60 (1995) 3020
16. Vedejs E., Fields S.C., Hayashi R., Hitchcock S.R., Powell D.R., and Schrimpf M.R. J. Am. Chem. Soc. 121 (1999) 2460
17. For review:. Petragnani N., and Stefani H.A. Tetrahedron 61 (2005) 1613
18. Petragnani N., and Comasseto J.V. Synthesis 793 (1991) 897
19. Comasseto J.V., Ling L.W., Petragnani N., and Stefani H.A. Synthesis (1997) 373
20. Zeni G., Braga A.L., and Stefani H.A. Acc. Chem. Res. 36 (2003) 731
21. Zeni G., Perin G., Cella R., Jacob R.G., Braga A.L., Silveira C.C., and Stefani H.A. Synlett 6 (2002) 975
22. Braga A.L., Lüdtke D.S., Vargas F., Donato R.K., Silveira C.C., Stefani H.A., and Zeni G. Tetrahedron Lett. 44 (2003) 1779
23. Braga A.L., Vargas F., Zeni G., Silveira C.C., and Andrade L.H. Tetrahedron Lett. 43 (2002) 4399
24. Zeni G., and Comasseto J.V. Tetrahedron Lett. 40 (1999) 4619
25. Nishibayashi Y., Cho C.-S., Ohe K., and Uemura S. J. Organomet. Chem. 507 (1996) 197
26. Nishibayashi Y., Cho C.-S., Ohe K., and Uemura S. J. Organomet. Chem. 526 (1996) 335
27. Stefani H.A., Cella R., Dörr F.A., Pereira C.M.P., Zeni Jr. G., and Gomes M. Tetrahedron Lett. 46 (2005) 563
28. Cella R., Cunha R.L.O.R., Reis A.E.S., Pimenta D.C., Klitzke C.F., and Stefani H.A. J. Org. Chem. 71 (2006) 244-250
29. Cella R., and Stefani H.A. Tetrahedron 62 (2006) 5656
30. Margulis M.A. High Energ. Chem. 38 (2004) 135
31. Mason T.J. Chem. Soc. Rev. 26 (1997) 443
32. Stefani H.A., Cella R., Dörr F.A., Pereira C.M.P., Gomes F.P., and Zeni G. Tetrahedron Lett. 46 (2005) 2001
33. Pereira C.M.P., Stefani H.A., Almeida R.B., Braga R.C., Guzen K.P., and Cella R. Tetrahedron Lett. 46 (2005) 6833
34. Stefani H.A., Oliveira C.B., Almeida R.B., Pereira C.M.P., Braga R.C., Cella R., Borges V.C., Savegnago L., and Nogueira C.W. J. Eur. Med. Chem. 41 (2006) 513
35. Bestmann H.J., and Vostrowsky O. Top. Curr. Chem. 109 (1983) 85
36. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863
37. Kelly S.E. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 1 (1991), Pergamon Press, Oxford 729
38. Petasis N.A., and Hu Y.H. Curr. Org. Chem. 1 (1997) 249
39. Shen Y.C. Acc. Chem. Res. 31 (1998) 584
40. For recent reviews, see:. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
41. Furstner A. Angew. Chem., Int. Ed. 39 (2000) 3013
42. Farina V., Krishnamurthy V., and Scott W.J. Org. React. (NY) 50 (1997) 1
43. Negishi E., and Liu F. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH 1-47
44. 4 and concentrated under vacuum. Purification by silica gel chromatography (eluting with hexane) yielded (Z,E)-1,4-diphenylbuta-1,3-diene (3a) in 84%.