Polymer cocktail: A multitask supported ionic liquid-like species to facilitate multiple and consecutive C-C coupling reactions

Advanced Synthesis and Catalysis

Volumn 352, Issue 17, 2010, Pages 3013-3021

  Sans, Victor ^c   Gelat, Fabien ^a   Karbass, Naima ^a   Burguete, M Isabel ^a   García Verdugo, Eduardo ^a,b   Luis, Santiago V ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^c UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

C C coupling reactions; green chemistry; ionic liquids; polymer supported reagents and catalysts; supported catalysts; supported ionic liquids

Indexed keywords

EID: 78649555273     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000528     Document Type: Article

References (53)

1. J. A. Gladysz, Pure Appl. Chem. 2001, 73, 1319-1324.
2. Immobilized Catalysts: Solid Phases, Immobilization and Applications, (Eds.:, A. Kirschning, W. Bannwarth, D.E. Bergbreiter, B. Desai,), in: Topics in Current Chemistry, Springer-Verlang, Berlin, Heidelberg, 2004.
3. The Power of Functional Resins in Organic Synthesis, (Eds.:, F. Albericio, J. Tulla-Puche,), Wiley-VCH, Weinheim, 2008.
4. Reviews and specials issues
5. P. H. Toy, M. Shi, (Eds.), Polymer-Supported Reagents and Catalysts: Increasingly Important Tools for Organic Synthesis, Tetrahedron 2005, 61, 12013-12192
6. J. A. Gladysz, (Ed.), Recoverable Catalysts and Reagents, Chem. Rev. 2002, 102, special issue
7. T. Kehat, K. Goren, M. Portnoy, New J. Chem. 2007, 31, 1218- 1242
8. J. Lu, P. H. Toy, Chem. Rev. 2009, 109, 815-838.
9. B. Altava, M. I. Burguete, E. García-Verdugo, S. V. Luis, M. J. Vicent, J. A. Mayoral, React. Funct. Polym. 2001, 48, 25-35
10. B. Altava, M. I. Burguete, J. M. Fraile, J. I. Garcia, S. V. Luis, J. A. Mayoral, S. V. Luis, Angew. Chem. 2000, 112, 1563-1566
11. Angew. Chem. Int. Ed. 2000, 39, 1503-1506.
12. T. Y. S. But, Y. Tashino, H. Togo, P. H. Toy, Org. Biomol. Chem. 2005, 3, 970-971.
13. N. T. S. Phan, C. S. Gill, J. V. Nguyen, Z. J. Zhang, C. W. Jones, Angew. Chem. 2006, 118, 2267-2270
14. Angew. Chem. Int. Ed. 2006, 45, 2209-2212.
15. M. I. Burguete, A. Cornejo, E. García-Verdugo, J. García, M. J. Gil, S. V. Luis, V. Martínez-Merino, J. A. Mayoral, M. Sokolova, Green Chem. 2007, 9, 1091-1096
16. N. Madhavan, C. W. Jones, M. Weck, Acc. Chem. Res. 2008, 41, 1153-1165.
17. Metal-Catalyzed Cross-Coupling Reactions, Vols. 1 and 2, (Eds.:, A. deMeijere, F. Diederich,), Wiley-VCH, Weinheim, 2004
18. Transition Metals for Organic Synthesis; Building Blocks and Fine Chemicals, (Ed.:, M. Beller,), Wiley-VCH, Weinheim, 2004.
19. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922.
20. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173.
21. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485-493.
22. J. M. Richardson, C. W. Jones, J. Catal. 2007, 251, 80-93
23. M. Weck, C. W. Jones, Inorg. Chem. 2007, 46, 1865-1875.
24. N. T. S. Phan, M. V. D. Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679.
25. E. J. Flahive, B. L. Ewanicki, N. W. Sach, S. A. O'Neill-Slawecki, N. S. Stankovic, S. Yu, S. M. Guinness, J. Dunn, Org. Process Res. Dev. 2008, 12, 637-645.
26. The specifications for low metal content in the final product (e.g., as low as <10ppm for palladium in an orally administered drug substance) require efficient separations processes for removal of dissolved metals from reaction mixtures. European Medicines Agency, Guideline on the Specification Limits for Residues of Metals Catalysts, January, 2007;.
27. P. Wasserscheid, T. Welton, (Eds.), Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2007.
28. N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123-150.
29. D. Zhao, Z. Fei, T. J. Geldbach, R. Scopelliti, P. J. Dyson, J. Am. Chem. Soc. 2004, 126, 15876-15882
30. P. Migowski, J. Dupont, Chem. Eur. J. 2007, 13, 32-39
31. X. Yang, Z. Fei, D. Zhao, W. Han Ang, Y. Li, Paul J. Dyson, Inorg. Chem. 2008, 47, 3292-3297
32. M. Ruta, G. Laurenczy, P. J. Dyson, L. Kiwi-Minsker, J. Phys. Chem. C, 2008, 112, 17814-17819
33. E. Redel, R. Thomann, C. Janiak, Chem. Commun. 2008, 1789-1791.
34. C. P. Mehnert, Chem. Eur. J. 2004, 11, 50-56
35. A. Riisager, R. Fehrmann, S. Flicker, R. vanHal, M. Haumann, P. Wasserscheid, Angew. Chem. 2005, 117, 826-830
36. Angew. Chem. Int. Ed. 2005, 44, 815-819
37. Y. Gu, G. Li, Adv. Synth. Catal. 2009, 351, 817-847.
38. P. Lozano, E. García-Verdugo, R. Piamtongkam, N. Karbass, T. DeDiego, M. I. Burguete, S. V. Luis, J. L. Iborra, Adv. Synth. Catal. 2007, 349, 1077-1084
39. M. I. Burguete, H. Erythropel, E. Garcia-Verdugo, S. V. Luis, V. Sans, Green Chem. 2008, 10, 401-407
40. W. Gil., K. Boczoń, A. M. Trzeciak, J. J. Ziół kowski, E. Garcia-Verdugo, S. V. Luis, V. Sans, J. Mol. Cat. A: Chem. 2009, 309, 131-136.
41. M. I. Burguete, F. Galindo, E. García-Verdugo, N. Karbass, S. V. Luis, Chem. Commun. 2007, 3086-3088.
42. B. Altava, M. I. Burguete, E. Garcia-Verdugo, N. Karbass, S. V. Luis, A. Puzary, V. Sans, Tetrahedron Lett. 2006, 47, 2311-2314
43. N. Karbass, V. Sans, E. Garcia-Verdugo, M. I. Burguete, S. V. Luis, Chem. Commun. 2006, 3095-3097
44. M. I. Burguete, E. García-Verdugo, F. Gelat, S. V. Luis, V. Sans, I. García-Villar, P. Licence, J. Catal. 2010, 269, 150-160.
45. A. H. M. deVries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. deVries, Org. Lett. 2003, 5, 3285-3288
46. A. Alimardanov, L. Schmieder-van de Vondervoort, A. H. M. deVries, J. G. deVries, Adv. Synth. Catal. 2004, 346, 1812-1817.
47. A. H. M. deVries, F. J. Parlevliet, L. Schmieder-van deVondervoort, J. H. M. Mommers, H. J. W. Henderickx, M. A. M. Walet, J. G. deVries, Adv. Synth. Catal. 2002, 344, 996-1002.
48. There are only few reports in the literature where catalyst and base are bearing in the same material
49. A. Corma, H. Garcia, A. Primo, J. Catal. 2006, 241, 123
50. F. Chen, K. Toh, S. Shen, G. J. Gan, Catal. Commun. 2007, 8, 405-409
51. A. Corma, H. Garcia, A. Leyva, A. Primo, Appl. Catal. A: General, 2004, 257, 77-83.
52. [23b]
53. G. A. Leeke, R. C. D. Santos, B. Al-Duri, J. P. K. Seville, C. J. Smith, C. K. Y. Lee, A. B. Holmes, I. F. McConvey, Org. Process Res. Dev. 2007, 11, 144-148.