A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs: A superior alternative to the Cadiot-Chodkiewicz reaction

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3687-3689

  Negishi, Ei Ichi ^a   Hata, Mitsuhiro ^a   Xu, Caiding ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND; PALLADIUM; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ALKYNES; CATALYSIS; INDICATORS AND REAGENTS; ORGANOMETALLIC COMPOUNDS; PALLADIUM; ZINC;

EID: 0034676530     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000270m     Document Type: Article

References (23)

1. (a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819.
2. (b) Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 597-647.
3. (c) Brandsma L.; Vasilevski, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, 1999; pp 49-105.
4. For other syntheses of conjugated diynes via stoichiometric or catalytic alkynyl-alkynyl coupling, see: (a) Sinclair, J. A.; Brown, H. C. J. Org. Chem. 1976, 41, 1078.
5. (b) Pelter, A.; Hughes, R.; Smith, K.; Tabata, M. Tetrahedron Lett. 1976, 4385.
6. (c) Zweifel, G.; Stracker, E. C. Tetrahedron Lett. 1990, 31, 6815.
7. (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977.
8. (e) Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 2053.
9. (f) Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763.
10. Negishi, E.; Okukado, N.; Lovich, S. F.; Luo, F. T. J. Org. Chem. 1984, 49, 2629.
11. For a subsequent related study, see: Kende, A. S.; Smith, C. A. J. Org. Chem. 1988, 53, 2655.
12. Kuhnt, D.; Anke, T.; Besl, H.; Bross, M.; Herrmann, R.; Mocek, U.; Steffan, B.; Steglich, W. J. Antibiot. 1990, 43, 1413.
13. Negishi, E.; Alimardanov, A.; Xu, C. Org. Lett. 2000, 2, 65.
14. Fairbrother, J. R. F.; Jones, E. R. H.; Thaller, V. J. Chem. Soc. C 1967, 1035.
15. Although no information about the two possible symmetrical diynes was given in the paper, the results and the experimental description suggest their formation to significant extents.
16. 4, and concentrated. Purification by column chromatography (silica gel, pentane) afforded 1.46 g (86%) of the title product [Kodaira, K.; Okuhara, K. Bull. Chem. Soc. Jpn. 1988, 61, 1625] as a colorless liquid,
17. 4, and concentrated. Purification by column chromatography (silica gel, pentane) afforded 1.46 g (86%) of the title product [Kodaira, K.; Okuhara, K. Bull. Chem. Soc. Jpn. 1988, 61, 1625] as a colorless liquid,
18. 4, and concentrated. Purification by column chromatography (silica gel, pentane) afforded 152 mg (72%) of the title product [Ziegler, C. B.; Harris, S. M.; Baldwin, J. E. J. Org. Chem. 1987, 52, 443]. Representative Procedure Using (E)-Bromoiodoethylene (Procedure B).
19. 2 (270 mg, 1.2 mmol) in THF (1 mL), and warmed to 0 °C. The reaction of 1,3-decadiynylzinc bromide thus generated with iodobenzene (1.0 mmol) was performed as described in Procedure A to give 189 mg (90%) of the title compound.
20. For other syntheses of conjugated diynes via 1,3-diynes and their derivatives, see: (a) Adams, S.; Potts, K. T. Synthesis 1988, 375.
21. (b) De Graaf, W.; Smits, A.; Boersma, J.; Van Koten, G.; Hoekstra, W. P. M. Tetrahedron 1988, 44, 6699.
22. (c) Löffler, A.; Himbert, G. Synthesis 1991, 232.
23. (d) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1995, 36, 3687.