Polystyrene-supported zinc bromide-ethylenediamine complex as a reusable and highly efficient heterogeneous catalyst for the synthesis of α,β-acetylenic ketones

Synthesis

Volumn , Issue 2, 2011, Pages 325-329

  Keivanloo, Ali ^a   Bakherad, Mohammad ^a   Bahramian, Bahram ^a   Rahmani, Mahrokh ^a   Taheri, Sayed Ali Naghi ^a  

^a SHAHROOD UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

acid chlorides; alkynes; cross coupling; heterogeneous catalysis; ketones

Indexed keywords

ACETYLENIC KETONES; ACID CHLORIDES; ALKYNES; CROSS-COUPLINGS; EFFICIENT SYNTHESIS; ETHYLENEDIAMINE COMPLEXES; HETEROGENEOUS CATALYSIS; HETEROGENEOUS CATALYST; REACTION CONDITIONS; TERMINAL ALKYNE; ZINC BROMIDE;

ACETYLENE; BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; POLYSTYRENES; SYNTHESIS (CHEMICAL); ZINC;

KETONES;

ALKYNE DERIVATIVE; CHLORINE; ETHYLENEDIAMINE; KETONE DERIVATIVE; POLYSTYRENE; ZINC BROMIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL LIBRARY; CROSS COUPLING REACTION; SYNTHESIS;

EID: 78650991814     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258365     Document Type: Article

References (46)

1. Karpov A S., Mller T J. J., Org. Lett. 2003 5 3451
2. Van den Hoven B G., El Ali B, Alper H, J. Org. Chem. 2000 65 4131
3. Wang X.-J, Tan J, Zhang L, Org. Lett. 2000 2 3107
4. Kel'in A V., Sromek A W., Gevorgyan V, J. Am. Chem. Soc. 2001 123 2074
5. Bagley M C., Hughes D D., Lloyd R, Powers V E. C., Tetrahedron Lett. 2001 42 6585
6. Bagley M C., Hughes D D., Taylor P H., Synlett 2003 259
7. Karpov A S., Merkul E, Oeser T, Mller T J. J., Chem. Commun. 2005 2581
8. Waldo J P., Larock R C., Org. Lett. 2005 7 5203
9. Karpov A S., Merkul E, Oeser T, Mller T J. J., Eur. J. Org. Chem. 2006 13 2991
10. Zhou C, Dubrovsky A V., Larock R C., J. Org. Chem. 2006 71 1626
11. Tohda Y, Sonogashira K, Hagihara N, Synthesis 1977 777
12. Walton D R. M., Waugh F, J. Organomet. Chem. 1972 37 45
13. Newman H, J. Org. Chem. 1973 38 2254
14. Yadav J S., Reddy B V. S., Reddy M S., Synlett 2003 1722
15. Wang J.-X, Wei B, Hu Y, Liu Z, Fu Y, Synth. Commun. 2001 31 3527
16. Cox R J., Ritson D J., Dane T A., Berge J, Charmant J P. H., Kantacha A, Chem. Commun. 2005 1037
17. Chen L, Li C.-J, Org. Lett. 2004 6 3151
18. Guo M, Li D, Zhang Z, J. Org. Chem. 2003 68 10172
19. Davis R B., Scheiber D H., J. Am. Chem. Soc. 1956 78 1675
20. Normant J F., Synthesis 1972 63
21. Logue M W., Moore G L., J. Org. Chem. 1975 40 131
22. Bourgain M, Normant J F., Bull. Soc. Chim. Fr. 1973 2137
23. Fontaine M, Chauvelier J, Barchewitz P, Bull. Soc. Chim. Fr. 1962 2145
24. Compagnon P L., Grosjean B, Lacour M, Bull. Soc. Chim. Fr. 1975 779
25. Yashina O G., Zarva T V., Vereshchagin L I., Zh. Org. Khim. 1967 3 219; Chem. Abstr. 1967, 66, 94664g
26. Vereshchagin L I., Yashina O G., Zarva T V., Zh. Org. Khim. 1966 2 1895; Chem. Abstr. 1967, 66, 46070p
27. Walton D R. M., Waugh F, J. Organomet. Chem. 1972 37 45
28. Logue M W., Teng K, J. Org. Chem. 1982 47 2549
29. Mohamed Ahmed M S., Mori A, Org. Lett. 2003 5 3057
30. McNamara C A., Dixon M J., Bradley M, Chem. Rev. 2002 102 3275
31. Clapham B, Reger T S., Janda K D., Tetrahedron 2001 57 4637
32. de Miguel Y R., Brule E, Margue R G., J. Chem. Soc., Perkin Trans. 1 2001 3085
33. Nishio R, Sugiura M, Kobayashi S, Chem. Asian J. 2007 2 983
34. Ye Z.-W, Yi W.-B, J. Fluorine Chem. 2008 129 1124
35. Chen L, Hong S, Zhou X, Zhou Z, Hou H, Catal. Commun. 2008 9 2221
36. Bakherad M, Keivanloo A, Bahramian B, Hashemi M, Tetrahedron Lett. 2009 50 1557
37. Bakherad M, Keivanloo A, Bahramian B, Mihanparast S, Tetrahedron Lett. 2009 50 6418
38. Bakherad M, Keivanloo A, Bahramian B, Rajaie M, Tetrahedron Lett. 2010 51 33
39. Bakherad M, Amin A H., Keivanloo A, Bahramian B, Raessi M, Chin. Chem. Lett. 2010 21 656
40. Chen J.-Y, Lin T.-C, Chen S.-C, Chen A.-J, Mou C.-Y, Tsai F.-Y, Tetrahedron 2009 65 10134
41. Palimkar S S., Kumar P H., Jogdand N R., Daniel T, Lahoti R J., Srinivasan K V., Tetrahedron Lett. 2006 47 5527
42. Fukuyama T, Yamaura R, Ryu I, Can. J. Chem. 2005 83 711
43. Hao W, Sha J, Sheng S, Cai M, J. Mol. Catal. A: Chem. 2009 298 94
44. Liang B, Huang M, You Z, Xiong Z, Lu K, Fathi R, Chen J, Yang Z, J. Org. Chem. 2005 70 6097
45. Wang B, Bonin M, Micouin L, Org. Chem. 2005 70 6126
46. Nishihara Y, Saito D, Inoue E, Okada Y, Miyazaki M, Inoue Y, Takagi K, Tetrahedron Lett. 2010 51 306