Carbon-carbon bond formation via homocoupling reaction of substrates with a broad diversity in water using Pd(OAc)2 and agarose hydrogel as a bioorganic ligand, support and reductant

Journal of Molecular Catalysis A: Chemical

Volumn 348, Issue 1-2, 2011, Pages 94-99

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Kazemi, Faezeh ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Agarose hydrogel; Aryl halide; Homocoupling; Palladium; Water

Indexed keywords

AGAROSE; ARYL HALIDES; CARBON-CARBON BOND FORMATION; CATALYTIC SYSTEM; COSOLVENTS; HIGH YIELD; HOMOCOUPLING; HOMOCOUPLING REACTIONS; ICP ANALYSIS; PHENYLACETYLENES; PHENYLBORONIC ACIDS; PHOSPHORUS LIGANDS; REACTION MEDIA; REDUCTANTS;

ACETYLENE; AROMATIC HYDROCARBONS; CATALYSTS; HYDROGELS; LEACHING; LIGANDS; METAL HALIDES; ORGANIC ACIDS; PALLADIUM; PHOSPHORUS; REDUCING AGENTS; STYRENE; WATER;

CARBON;

EID: 80052965791     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2011.08.010     Document Type: Article

References (63)

1. V. Penalva, J. Hassan, L. Lavenot, C. Gozzi, and M. Lemaire Tetrahedron Lett. 39 1998 2559 2560
2. W.M. Seganish, M.E. Mowery, S. Riggleman, and P. Deshong Tetrahedron 61 2005 2117 2121
3. H.S. He, C. Zhang, C.K.W. Ng, and P.H. Toy Tetrahedron 61 2005 12053 12057
4. N. Ma, Z. Duan, and Y. Wu J. Organomet. Chem. 691 2006 5709 5712
5. F. Ullman, and Ber. Bunsen Phys. Chem. 36 1903 2389
6. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
7. R. Bedford, C.S.J. Cazin, M.B. Hursthose, M.E. Light, and V.J.M. Scordia Dalton Trans. 2004 3864 3868
8. R. Bedford, C.S.J. Cazin, and D. Holder Coord. Chem. Rev. 248 2004 2283 2321
9. R.B. Bedford Chem. Commun. 21 2003 1787 1796
10. U. Nettekoven, F. Naud, A. Schnyder, and H.U. Blaser Synlett 2004 2549 2552
11. O. Navarro, N. Marion, Y. Oonishi, R.A. Kelly III, and S.P. Nolan J. Org. Chem. 71 2006 685 692
12. V. Cal, A. Nacci, and A. Monopoli Eur. J. Org. Chem. 17 2006 3791 3802
13. C.C. Cassol, A.P. Umpierre, G. Machado, S.I. Wolke, and J. Dupont J. Am. Chem. Soc. 127 2005 3298 3299
14. V. Cal, A. Nacci, A. Monopoli, and F. Montigelli J. Org. Chem. 70 2005 6040 6044
15. G.A. Grasa, M.S. Viciu, J. Huang, and S.P. Nolan J. Org. Chem. 66 2001 7729 7737
16. A. Corma, H. Garcia, and A. Leyva Tetrahedron 60 2004 8553 8560
17. N. Iranpoor, H. Firouzabadi, A. Tarassoli, and M. Fereidoonnezhah Bull. Chem. Soc. Jpn. 83 2010 1367 1373
18. M. Kuroboshi, Y. Waki, and H. Tanaka J. Org. Chem. 68 2003 3938 3942
19. C. Liu, L. Jin, and A. Lei Synlett 2010 2527 2536
20. A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, and H. Yamamoto J. Org. Chem. 57 1992 6386 6387
21. B.C. Rann, P. Dutta, and A. Sarkar Tetrahedron Lett. 39 1998 9557 9558
22. Y.L. Hu, F. Li, G.L. Gu, and M. Lu Catal. Lett. 141 2011 467 473
23. N.G. Willis, and J. Guzman Appl. Catal. A 339 2008 68 75
24. S. Carrettin, A. Corma, and M. Lglesias Appl. Catal. A 291 2005 247 252
25. A. Benameur, T. Boumoud, B. Boumoud, and S. Rhouati Eur. J. Org. Chem. 7 2010 1196 1199
26. P. Anastas, and M. Kirchhoff Acc. Chem. Res. 35 2002 686 694
27. R.A. Sheldon Chemtech 24 1994 38 47
28. C. Jimenez-Gonzalez, A.D. Curzons, D.J.C. Constable, and V. Cunningham Int. J. LCA 9 2004 114 121
29. H. Firouzabadi, N. Iranpoor, and M. Abbasi Adv. Synth. Catal. 351 2009 755 766
30. H. Firouzabadi, N. Iranpoor, and M. Gholinejad Tetrahedron 65 2009 7079 7084
31. H. Firouzabadi, N. Iranpoor, and A. Garzan Adv. Synth. Catal. 347 2005 1925 1928
32. H. Firouzabadi, N. Iranpoor, A.A. Jafari, and E. Riazymontazer Adv. Synth. Catal. 348 2006 434 438
33. H. Firouzabadi, N. Iranpoor, and F. Nowrouzi Chem. Commun. 2005 789 791
34. H. Firouzabadi, N. Iranpoor, and A. Khoshnood J. Mol. Catal. A: Chem. 274 2007 109 115
35. H. Firouzabadi, N. Iranpoor, and M. Abbasi Tetrahedron 65 2009 5293 5301
36. H. Firouzabadi, N. Iranpoor, and M. Gholinejad J. Mol. Catal. A 321 2010 110 116
37. H. Firouzabadi, N. Iranpoor, and M. Gholinejad Adv. Synth. Catal. 352 2010 119 124
38. H. Firouzabadi, N. Iranpoor, M. Gholinejad, and J. Hoseini Adv. Synth. Catal. 353 2011 125 132
39. H. Firouzabadi, N. Iranpoor, A. Ghaderi, M. Ghavami, and S.J. Hoseini Bull. Chem. Soc. Jpn. 84 2011 100 109
40. C.A. Fleckenstein, and H. Plenio Green Chem. 9 2007 1287 1291
41. C.A. Fleckenstein, and H. Plenio J. Org. Chem. 73 2008 3236 3244
42. B. Karimi, D. Elhamifar, J.H. Clark, and A.J. Hunt Chem. Eur. J. 16 2010 8047 8053
43. T. Nishikata, and B.H. Lipshutz J. Am. Chem. Soc. 131 2009 12103 12105
44. A. Krasovskiy, C. Duplais, and B.H. Lipshutz Org. Lett. 12 2010 4742 4744
45. C. Duplais, A. Krasovskiy, A. Wattenberg, and B.H. Lipshutz Chem. Commun. 46 2010 562 564
46. B.H. Lipshutz, T.B. Petersen, and A.R. Abela Org. Lett. 10 2008 1333 1336
47. M. Kurooshi, Y. Waki, and H. Tanaka J. Org. Chem. 68 2003 3938 3942
48. C. Araki Bull. Chem. Soc. Jpn. 29 1956 543 544
49. C. Yang, and S.P. Nolan J. Org. Chem. 67 2002 591
50. K.H. Shaughnessy, and R.B. DeVasher Curr. Org. Chem. 9 2005 585 604
51. K.H. Shaughnessy Chem. Rev. 109 2009 643 710
52. G.W. Kabalka, L. Wang, R.M. Pagni, C.M. Hair, and V. Namboodiri Synthesis 2003 217 222
53. D.J. Koza, and E. Carita Synthesis 2002 2183 2186
54. S. Chen, J. Zhang, Y.H. Li, J. Wen, S.Q. Bian, and X.Q. Yu Tetrahedron Lett. 50 2009 6795 6797
55. E.S. Yoo J. Adv. Eng. Technol. 2009 345 347
56. M.A. Ogliaruso, L.A. Shadoff, and E.I. Becker J. Org. Chem. 28 1963 2725 2728
57. S. Padmanabhau, K.V. Gavaskar, and D.J. Triggle Synth. Commun. 26 1996 3109 3113
58. G. Lunn J. Org. Chem. 57 1992 6317
59. Y. Xie, G.K. Tan, Y.K. Yan, J.J. Vittal, S.Ch. Ng, and T.S.A. Hor J. Chem. Soc. Dalton Trans. 1999 773 779
60. S.E. Denmark, and M.H. Ober Org. Lett. 5 2003 1357 1360
61. K. Yin, C. Li, J. Li, and X. Jia Appl. Organomet. Chem. 25 2011 16 20
62. H. Firouzabadi, N. Iranpoor, and A. Ghaderi Org. Biomol. Chem. 9 2011 865 871
63. R.A. Sheldon, M. Wallau, I.W.C.E. Arends, and U. Schuchardt Acc. Chem. Res. 31 1998 485 488