Palladium supported on natural phosphate: Catalyst for Suzuki coupling reactions in water

Applied Catalysis A: General

Volumn 450, Issue , 2013, Pages 13-18

  Hassine, Ayoub ^a   Sebti, Saïd ^a   Solhy, Abderrahim ^b   Zahouily, Mohamed ^b,e   Len, Christophe ^c   Hedhili, Mohamed Nejib ^d   Fihri, Aziz ^b,d  

^a FACULTÉ DES SCIENCES BEN M SIK   (Morocco)

^b MAScIR Foundation   (Morocco)

^c UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

^d KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

^e HASSAN II UNIVERSITY   (Morocco)

Author keywords

Natural phosphate; Palladium; Supported catalysts; Suzuki coupling reactions

Indexed keywords

20TH CENTURY; ARYL CHLORIDE; CATALYTIC REACTIONS; ECOLOGICAL RELEVANCE; NATURAL PHOSPHATE; PHASE TRANSFER; REACTION MEDIUM; SUZUKI COUPLING REACTION; SUZUKI-MIYAURA COUPLING REACTION; TURNOVER NUMBER;

CATALYSIS; CATALYST SUPPORTS; CATALYSTS; CHLORINE COMPOUNDS; ORGANIC SOLVENTS; PALLADIUM; PHOSPHATE DEPOSITS;

LOADING;

EID: 84872338399     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2012.09.046     Document Type: Article

References (60)

1. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
2. A. Fihri, P. Meunier, and J.C. Hierso Coord. Chem. Rev. 251 2007 2017 2055
3. A.C. Hillier, G.A. Grasa, M.S. Viciu, H.M. Lee, C. Yang, and S.P. Nolan J. Organomet. Chem. 653 2002 69 82
4. G.A. Grasa, M.S. Viciu, J. Huang, C. Zhang, M.L. Trudell, and S.P. Nolan Organometallics 21 2002 2866 2873
5. R.F. Heck, and J.P. Nolly J. Org. Chem. 37 1972 2320 2322
6. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467 4470
7. A.O. King, N. Okukado, and E. Negishi J. Chem. Soc. Chem. Commun. 1977 683 684
8. A.O. King, E. Negishi, F.J. Villani Jr., and A. Silveira Jr. J. Org. Chem. 43 1978 358 360
9. N. Miyaura, T. Yanagi, and A. Suzuki Synth. Commun. 11 1981 513 519
10. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
11. J.L. Malleron, J.C. Fiaud, and J.Y. Legros Handbook of Palladium Organic Reactions 1997 Academic Press San Diego
12. V.V. Grushin, and H. Alper S. Murai, Activation of Unreactive Bonds and Organic Synthesis 1999 Springer Berlin 193
13. V.V. Grushin, and H. Alper Chem. Rev. 94 1994 1047 1062
14. C. Vargas, A.M. Balu, J.M. Campelo, C. Gonzalez-Arellano, R. Luque, and A.A. Romero Curr. Org. Synth. 7 2010 568 586
15. V.L. Budarin, P.S. Shuttleworth, J.H. Clark, and R. Luque Curr. Org. Synth. 7 2010 614 627
16. Y. Masuyama, Y. Sugioka, S. Chonan, N. Suzuki, M. Fujita, K. Hara, and A. Fukuoka J. Mol. Catal. A: Chem. 352 2012 81 85
17. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, and J.M. Basset Chem. Rev. 111 2011 3036 3075
18. G. Marck, A. Villiger, and R. Buchecker Tetrahedron Lett. 35 1994 3277 3280
19. C.R. LeBlond, A.T. Andrews, Y. Sun, and J.R. Sowa Org. Lett. 3 2001 1555 1557
20. F.X. Felpin J. Org. Chem. 70 2005 8575 8578
21. G. Zhang Synthesis 2005 537 542
22. V. Polshettiwar, C. Len, and A. Fihri Coord. Chem. Rev. 253 2009 2599 2626
23. S. Minakata, and M. Komatsu Chem. Rev. 109 2009 711 724
24. R. Haag, and S. Roller Top. Curr. Chem. 242 2004 1 42
25. Y. Uozumi Top. Curr. Chem. 242 2004 77 112
26. N.E. Leadbeater, and M. Marco Chem. Rev. 102 2002 3217 3274
27. S. Alesi, F. Di Maria, M. Melucci, D.J. Macquarrie, R. Luque, and G. Barbarella Green Chem. 10 2008 517 523
28. V.L. Budarin, J.H. Clark, R. Luque, D.J. Macquarrie, and R.J. White Green Chem. 10 2008 382 387
29. M.J. Gronnow, R. Luque, D.J. Macquarrie, and J.H. Clark Green Chem. 7 2005 552 557
30. S. Sebti, H. Boukhal, N. Hanafi, and S. Boulaajaj Tetrahedron Lett. 40 1999 6207 6209
31. S. Sebti, A. Rhihil, A. Saber, and N. Hannafi Tetrahedron Lett. 37 1996 6555 6556
32. S. Sebti, A. Saber, A. Rhihil, R. Nazih, and R. Tahir Appl. Catal. A 206 2001 217 220
33. R. Tahir, K. Banert, and S. Sebti Appl. Catal. A 298 2006 261 264
34. J.M. Fraile, J.I. Garcia, J.A. Mayoral, S. Sebti, and R. Tahir Green Chem. 3 2001 271 274
35. A. Solhy, A. Smahi, H. El Badaoui, B. Elaabar, A. Amoukal, A. Tikad, S. Sebti, and D.J. Macquarrie Tetrahedron Lett. 44 2003 4031 4033
36. F. Bazi, H. El Badaoui, S. Tamani, S. Sokori, L. Oubella, M. Hamza, S. Boulaajaj, and S. Sebti J. Mol. Catal. A 256 2006 43 47
37. V. Polshettiwar, A. Decottignies, C. Len, and A. Fihri ChemSusChem 3 2010 502 522
38. A. Chanda, and V.V. Fokin Chem. Rev. 109 2009 725 748
39. V. Polshettiwar, and R.S. Varma Acc. Chem. Res. 41 2008 629 639
40. S. Sebti, A. Solhy, R. Tahir, A. Smahi, S. Boulaajaj, J.A. Mayoral, J.I. García, J.M. Fraile, A. Kossir, and H. Oumimoun J. Catal. 213 2003 1 6
41. M. Zahouily, M. Salah, B. Bahlaouane, A. Rayadh, A. Houmam, E.A. Hamed, and S. Sebti Tetrahedron 60 2004 1631 1635
42. M.C. Burrell, G.A. Smith, and J.J. Chera Surf. Interface Anal. 11 1988 160 164
43. O.B. Belskaya, I.G. Danilova, M.O. Kazakov, T.I. Gulyaeva, L.S. Kibis, A.I. Boronin, A.V. Lavrenov, and V.A. Likholobov Appl. Catal. A 387 2010 5 12
44. K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, and K. Kaneda J. Am. Chem. Soc. 124 2002 11572 11573
45. K. Mori, T. Hara, T. Mizugaki, K. Ebitani, and K. Kaneda J. Am. Chem. Soc. 126 2004 10657 10666
46. A.F. Littke, and G.C. Fu Angew. Chem. Int. Ed. 41 2002 4176 4211
47. A. Zapf, A. Ehrentraut, and M. Beller Angew. Chem. Int. Ed. 39 2000 4153 4155
48. A.F. Littke, C. Dai, and G.C. Fu J. Am. Chem. Soc. 122 2000 4020 4028
49. J.H. Kirchhoff, C. Dai, and G.C. Fu Angew. Chem. Int. Ed. 41 2002 1945 1947
50. J.P. Wolfe, and S.L. Buchwald Angew. Chem. Int. Ed. 38 1999 2413 2416
51. J.P. Wolfe, R.A. Singer, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9550 9561
52. B.J. Gallon, R.W. Kojima, R.B. Kaner, and P.L. Diaconescu Angew. Chem. Int. Ed. 46 2007 7251 7254
53. J. Gil-Moltó, S. Karlström, and C. Nájera Tetrahedron 61 2005 12168 12176
54. It has been demonstrated that the apatitic tricalcium phosphate acts as a useful solid for the supported aqueous phase catalysis in hydroformylation reaction. See: M. Dessoudeix, U.J. Jáuregui-Haza, M. Heughebaert, A.M. Wilhelm, H. Delmas, A. Lebugle, and P. Kalck Adv. Synth. Catal. 344 2002 406 412
55. N. Jamwal, M. Gupta, and S. Paul Green Chem. 10 2008 999 1003
56. M. Lysén, and K. Klaus Synthesis 4 2006 692 698
57. M. Lysén, and K. Klaus Synlett 11 2005 1671 1674
58. M.-J. Jin, and D.-H. Lee Angew. Chem. Int. Ed. 49 2010 1119 1122
59. Y. Mori, M. Tanemura, and S. Tanemura Appl. Surf. Sci. 228 2004 292 296
60. B.J. Tielsch, J.E. Fulghum, and D.J. Surman Surf. Interface Anal. 24 1996 459 468