Silica-supported zinc bromide (ZnBr2/SiO2): A highly efficient heterogeneous catalyst for coupling acid chlorides with terminal alkynes

Tetrahedron Letters

Volumn 52, Issue 13, 2011, Pages 1498-1502

  Keivanloo, Ali ^a   Bakherad, Mohammad ^a   Bahramian, Bahram ^a   Baratnia, Samaneh ^a  

^a SHAHROOD UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Heterogeneous; Supported catalyst; Terminal alkyne; Ynone

Indexed keywords

ALKYNE; CHLORIDE; KETONE DERIVATIVE; PHENYLACETYLENE; SILICON DIOXIDE; SOLVENT; ZINC BROMIDE;

ARTICLE; CATALYST; COMBINATORIAL CHEMISTRY; CROSS COUPLING REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 79951955824     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.101     Document Type: Article

References (38)

1. C.H. Fawcett, R.D. Firu, and D.M. Spencer Physiol. Plant Pathol. 1 1971 163
2. D. Mead, A.E. Asato, M. Denny, R.S.H. Liu, Y. Hanzawa, T. Taguchi, A. Yamada, N. Kobayashi, A. Hosoda, and Y. Kobayashi Tetrahedron Lett. 28 1987 259
3. C. Chowdhury, and N.G. Kundu Tetrahedron 55 1999 7011
4. C.A. Quesnelle, P. Gill, M. Dodier, D. St. Laurent, M. Serrano-Wu, A. Marinier, A. Martel, C.E. Mazzucco, T.M. Stickle, J.F. Barrett, D.M. Vyas, and B.N. Balasubramanian Bioorg. Med. Chem. Lett. 13 2003 519
5. W. Reid, and E. Koenig Justus Liebigs Ann. Chem. 24 1972 755
6. M. Hojo, K. Omita, and A. Hosomi Tetrahedron Lett. 34 1993 485
7. A. Arcadi, F. Marenelli, and E. Rossi Tetrahedron 55 1999 13233
8. A.V. Kelin, A.W. Sromek, and V. Gevorgyan J. Am. Chem. Soc. 123 2001 2074
9. A. Jeevnandan, K. Narkunan, and Y. Ling J. Org. Chem. 66 2001 6014
10. D.B. Grotjahn, S. Van, D. Combs, D.A. Lev, C. Schneider, M. Rideout, C. Meyer, G. Hernandez, and L. Mejorado J. Org. Chem. 67 2002 9200
11. A.S. Karpov, and T.J. Muller Org. Lett. 5 2003 3451
12. R.B. Davis, and D.H. Scheiber J. Am. Chem. Soc. 78 1956 1675
13. J.F. Normant Synthesis 1972 63
14. M.W. Logue, and G.L. Moore J. Org. Chem. 40 1975 131
15. M. Bourgain, and J.F. Normant Bull. Soc. Chim. Fr. 1973 2137
16. M. Fontaine, J. Chauvelier, and P. Barchewitz Bull. Soc. Chim. Fr. 1962 2145
17. P.L. Compagnon, B. Grosjean, and M. Lacour Bull. Soc. Chim. Fr. 1975 779
18. Yashina, O. G.; Zarva, T. V.; Vereshchagin, L. I. Zh. Org. Khim. 1967, 3, 219.
19. Chem. Abstr. 1967, 66, 94664g.
20. Vereshchagin, L. I.; Yashina, O. G.; Zarva, T. V. Zh. Org. Khim. 1966, 2, 1895.
21. Chem. Abstr. 1967, 66, 46070p.
22. D.R.M. Walton, and F. Waugh J. Organomet. Chem. 37 1972 45
23. M.W. Logue, and K. Teng J. Org. Chem. 47 1982 2549
24. C. Chowdhury, and N.G. Kundu Tetrahedron Lett. 37 1996 7323
25. J.-X. Wang, B. Wei, Y. Hu, Z. Liu, and Y. Fu Synth. Commun. 31 2001 3527
26. R.J. Cox, D.J. Ritson, T.A. Dane, J. Berge, J.P.H. Charmant, and A. Kantacha Chem. Commun. 2005 1037
27. L. Chen, and C.-J. Li Org. Lett. 6 2004 3151
28. M. Guo, D. Li, and Z. Zhang J. Org. Chem. 68 2003 10172
29. Y. Tohda, K. Sonogashira, and N. Hagihara Synthesis 1977 777
30. M. Bakherad, A. Keivanloo, B. Bahramian, and M. Hashemi Tetrahedron Lett. 50 2009 1557
31. M. Bakherad, A. Keivanloo, B. Bahramian, and S. Mihanparast Tetrahedron Lett. 50 2009 6418
32. M. Bakherad, A. Keivanloo, B. Bahramian, and M. Rajaie Tetrahedron Lett. 51 2010 33
33. K.Y. Lee, C.G. Lee, J.E. Na, and J.N. Kim Tetrahedron Lett. 46 2005 69
34. K.Y. Lee, M.J. Lee, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 665
35. K.Y. Lee, M.J. Lee, and J.N. Kim Tetrahedron 61 2005 8705
36. J.-Y. Chen, T.-C. Lin, S.-C. Chen, A.-J. Chen, C.-Y. Mou, and F.-Y. Tsai Tetrahedron 65 2009 10134
37. B. Liang, M. Huang, Z. You, Z. Xiong, K. Lu, R. Fathi, J. Chen, and Z. Yang J. Org. Chem. 70 2005 6097
38. D.A. Alonso, C. Najera, and M.C. Pacheco J. Org. Chem. 69 2004 1615