Amine- and phosphine-free palladium(II)-catalyzed homocoupling reaction of terminal alkynes

Tetrahedron

Volumn 61, Issue 7, 2005, Pages 1903-1907

  Li, Jin Heng ^a   Liang, Yun ^a   Zhang, Xu Dong ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

Homecoupling reaction; Palladium; Phosphine free; Terminal alkynes

Indexed keywords

ALKYNE; AMINE; CHLORINE DERIVATIVE; COPPER DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE; SODIUM DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 12944321352     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.12.026     Document Type: Article

References (38)

1. F. Bohlmann, F.T. Burkhart, and C. Zero Naturally Occurring Acetylenes 1973 Academic London and New York
2. L. Hansen, and P.M. Boll Phytochemistry 25 1986 285
3. Y.S. Kim, S.H. Jin, S.L. Kim, and D.R. Hahn Arch. Pharm. Res. 12 1989 207
4. H. Matsunaga, M. Katano, H. Yamamoto, H. Fujito, M. Mori, and K. Tukata Chem. Pharm. Bull. 38 1990 3480
5. For representative on homocoupling of alkynes, see (a) R.A. Raphael, E.C. Taylor, and H. Wynberg Advances in Organic Chemistry Vol. 4 1963 Mack Printing New York pp 225-328
6. H.G. Viehe Chemistry of Acetylene 1969 Marcel Dekker New York
7. W.S. Trahanovsky Oxidation in Organic Chemistry Vol. 5-B 1973 Academic New York
8. M. Hudlicky Oxidation in Organic Chemistry 1990 ACS Monograph 186 Washington DC p 58
9. K. Sonogashira B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon Oxford 551
10. P. Siemsen, R.C. Livingston, and F. Diederich Angew. Chem., Int. Ed. 39 2000 2632
11. E. Negishi, and A. Alimardanov E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 2002 Wiley-Interscience New York 989
12. C. Glaser Ber. Dtsch. Chem. Ges. 2 1869 422
13. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467
14. J. Li, and H. Jiang Chem. Commun. 1999 2369 and references cited therein
15. For palladium-catalyzed homocoupling reaction of alkynes, see: (a) R. Rossi, A. Carpita, and C. Bigelli Tetrahedron Lett. 26 1985 523
16. M. Vlassa, I. Ciocan-Tarta, F. Margineanu, and I. Oprean Tetrahedron 52 1996 1337
17. J. Li, A.W.-H. Mau, and C.R. Strauss Chem. Commun. 1997 1275
18. Q. Liu, and D.J. Burton Tetrahedron Lett. 38 1997 4371
19. H.-F. Chow, C.-W. Wan, K.-H. Low, and Y.-Y. Yeung J. Org. Chem. 66 2001 1910
20. A. Lei, M. Srivastava, and X. Zhang J. Org. Chem. 67 2002 1969
21. I.J.S. Fairlamb, P.S. Bäuerlein, L.R. Marrison, and J.M. Dickinson Chem. Commun. 2003 632
22. L.H. Pignolet Homogeneous Catalysis with Metal Phosphine Complexes 1983 Plenum New York
23. G.W. Parshall, and S. Ittel Homogeneous Catalysis 1992 Wiley New York
24. 13C NMR spectra, see: J.-H. Li, H.-F. Jiang, and M.-C. Chen J. Org. Chem. 66 2001 3627
25. For the papers on the use of amines as the ligands for the Pd(0) catalysts, see: (a) J.T. Link L.E. Overman Organic Reaction Vol. 60 2002 Wiley New Jersey
26. E.R. Strieter, D.G. Blackmond, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 13978
27. B. Tao, and D.W. Boykin J. Org. Chem. 69 2004 4330
28. B. Tao, and D.W. Boykin J. Org. Chem. 69 2004 4330
29. J.-H. Li, and W.-J. Liu Org. Lett. 6 2004 2809
30. G. Märkl, H. Hauptmann, and A. Merz J. Organomet. Chem. 249 1983 335
31. J.B. Armitage, E.R.H. Jones, and M.C. Whiting J. Chem. Soc. 1951 44
32. H.K. Black, D.H.S. Horn, and B.C.L. Weedon J. Chem. Soc. 1954 1704
33. H. Bock, and H. Seidl J. Chem. Soc. B 1968 1158
34. S.V. Damle, D. Seomoon, and P.H. Lee J. Org. Chem. 68 2003 7085
35. B. Wex, B.R. Kaafarani, A.G. Oliver, J.A.K. Bauer, and D.C. Neckers J. Org. Chem. 68 2003 8258
36. R.C. Larock, and S.A. Hershberger J. Org. Chem. 45 1980 3840
37. R.E. Maleczka Jr., L.R. Terrell, D.H. Clark, S.L. Whitehead, W.P. Gallagher, and I. Terstiege J. Org. Chem. 64 1999 5958
38. Generally, oxygen is an effective oxidant for the Cu(I)-catalyzed Glaser coupling reaction, see the Refs. 3-5.