A convenient route to unsymmetrical conjugated diynes

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2763-2766

  Alami, Mouâd ^a   Ferri, Fabiola ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

1 halogeno alkynes; copper; palladium; unsymmetrical 1,3 diynes

Indexed keywords

ALKYNE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029928723     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00414-5     Document Type: Article

References (20)

1. (a) Cadiot, P.; Chodkiewicz, W. in "Chemistry of Acetylenes", H. G. Viehe, Ed., Marcel Dekker, New York 1969, pp. 597.
2. (b) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819-869.
3. For alternative syntheses of unsymmetrical conjugated diynes see: (a) Müller, E.; Segnitz, A. Just. Lieb. Ann. Chem. 1973, 1583-1591.
4. (b) Pelter, A.; Hughes, R.; Smith, K.; Tabata, M. Tetrahedron Lett. 1976, 48, 4385-4388.
5. (c) Sinclair, J.A.; Brown, H.C. J. Org. Chem. 1976, 41, 1078-1079.
6. (d) Kende, A.S.; Smith, C.A. J. Org. Chem. 1988, 53, 2655-2657.
7. (e) Nye, S.A.; Potts, K.T. Synthesis 1988, 375-377.
8. (f) Stracker, E. C.; Zweifel, G. Tetrahedron Lett. 1990, 31, 6815-6818.
9. (g) Löffler, A.; Himbert, G. Synthesis 1991, 232-233.
10. (h) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1995, 36, 3687-3690 and references therein.
11. Negishi, E.; Okukado, N.; Lovich, S. F.; Luo, F. J. Org. Chem. 1984, 49, 2629-2632.
12. Without palladium catalyst, the coupling of preformed copper acetylides with 1-bromo alkynes has been reported to give corresponding diynes see: (a) Curtis, R.F., Taylor, J.A. J. Chem. Soc. 1971, 186-187.
13. (b) Miller, J.A.; Zweifel, G. Synthesis 1983, 128-130.
14. Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829-6839.
15. (a) Wityak, J.; Chan, J. B. Synth. Comm. 1991, 21, 977-979.
16. (b) Hoye, T.R.; Hanson, P.R. Tetrahedron Lett. 1993, 34, 5043-5046.
17. The efficiency of this amine for the cross coupling of vinyl and aryl halides or triflates with terminal alkynes has been recently reported, see: Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406.
18. Brandsma, L. "Preparative Acetylenic Chemistry"; 2nd Ed., Elsevier, 1988, pp. 212.
19. Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109-6112.
20. Satisfactory spectral data were obtained for all new compounds.