Pd catalysts immobilized onto gel-supported ionic liquid-like phases (g-SILLPs): A remarkable effect of the nature of the support

Journal of Catalysis

Volumn 269, Issue 1, 2010, Pages 150-160

  Burguete, M Isabel ^a   García Verdugo, Eduardo ^b   Garcia Villar, Ignacio ^c   Gelat, Fabien ^a   Licence, Peter ^c   Luis, Santiago V ^a   Sans, Victor ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^c UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

C C coupling; Catalysis; Functional polymers; Pd; Supported catalysts; Supported ionic liquid

Indexed keywords

C-C COUPLING; CATALYTIC ACTIVITY; CATALYTIC CYCLES; CATALYTIC SYSTEM; EXCELLENT PERFORMANCE; FUNCTIONAL SITES; FUNCTIONALIZED POLYMERS; HECK REACTIONS; HIGHER TEMPERATURES; KEY FACTORS; PD; PD CATALYST; PD SPECIES; PD-SUPPORTED CATALYSTS; POLYMERIC MATERIAL; RECYCLABILITY; SUPPORTED PD;

CATALYSIS; CATALYST ACTIVITY; CATALYST SUPPORTS; FUNCTIONAL POLYMERS; GELS; IONIZATION OF LIQUIDS; IONS; LEACHING; PALLADIUM; STRATEGIC PLANNING;

IONIC LIQUIDS;

EID: 77955093528     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2009.11.002     Document Type: Article

References (88)

1. Heck R.F. Acc. Chem. Res. 12 (1979) 146
2. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 12 (2000) 3009
3. M. Beller (Ed.), Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals, Wiley-VCH, Weinheim, 2004.
4. Hierso J.-C., Beaupérin M., and Meunier P. Chem. Eur. J. 13 (2007) 6908
5. de Vries A.H.M., Parlevliet F.J., Schmieder-van de Von-dervoort L., Mommers J.H.M., Henderickx H.J.W., Walet M.A.N., and de Vries J.G. Adv. Syn. Catal. 344 (2002) 996
6. de Vries A.H.M., Mulders J.M.C.A., Mommers J.H.M., Henderickx H.J.W., and de Vries J.G. Org. Lett. 5 (2003) 3285
7. de Vries J.G. Dalton Trans. 421 (2006)
8. For a general overview on metal nanoclusters and their applications in catalysis, see. Bradley J.S., Hill E., Leonowicz M.E., and Witzke H. J. Mol. Catal. 41 (1987) 59
9. Aiken III J.D., and Finke R.G. J. Mol. Catal. A 145 (1999) 1
10. Nnnemann H.B., and Richards R.M. Eur. J. Org. Chem. (2001) 2455
11. Yin L., and Liebscher J. Chem. Rev. 107 (2007) 133
12. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions vol. 1 (2004), Wiley-VCH, Weinheim
13. For the "Ideal Catalysts" concept see. Gladysz J.A. Pure Appl. Chem. 73 (2001) 1319
14. Bhanage B.M., and Arai M. Catal. Rev. 43 (2001) 315
15. Garret C.E., and Prasad K. Adv. Syn. Catal. 346 (2004) 889
16. Flahive E.J., Ewanicki B.L., Sach N.W., O'Neill-Slawecki S.A., Stankovic N.S., Yu S., Guinness S.M., and Dunn J. Org. Process Res. Dev. 12 (2008) 637
17. Polshettiwar V., and Molnár A. Tetrahedron 63 (2007) 6949
18. Phan N.T.S., Sluys M.V.D., and Jones C.W. Adv. Syn. Catal. 348 (2006) 609
19. Biffis A., Zecca M., and Basato M. J. Mol. Catal. A 173 (2001) 249
20. Yu K., Sommer W., Richardson J.M., Weck M., and Jones C.W. Adv. Syn. Catal. 347 (2005) 161
21. Sommer W., Yu K., Sears J.S., Ji J., Zheng X., Davis R.J., Sherill C.D., Jones C.W., and Weck M. Organometallics 24 (2005) 4351
22. Richardson J.M., and Jones C.W. J. Catal. 251 (2007) 80
23. Weck M., and Jones C.W. Inorg. Chem. 46 (2007) 1865
24. See monographic issue. Gladysz J.A. Chem. Rev. 102 (2002) 3215
25. In: Albericio F., and Tulla-Puche (Eds). J The Power of Functional Resins in Organic Synthesis (2008), Wiley-VCH, Weinheim
26. Altava B., Burguete M.I., Fraile J.M., García J.I., Luis S.V., Mayoral J.A., and Vicent M.J. Angew. Chem. Int. Ed. 39 (2000) 1506
27. Hagiwara H., Masahiro Y., Sugawara Y., Hoshi T., and Suzuki T. Chem. Commun. 23 (2005) 2942
28. Altava B., Burguete M.I., Garcia-Verdugo E., Luis S.V., and Vicent M.J. Green Chem. 8 (2006) 717
29. Madhavan N., Jones C.W., and Weck M. Acc. Chem. Res. 41 (2008) 1153
30. Helms B., Guillaudeu S.J., Xie Y., McMurdo M., Hawker C.J., and Fréchet J.M.J. Angew. Chem. Int. Ed. 44 (2005) 6384
31. Kwong C.K.-W., Huang ; R., Zhang M., Shi H., and Toy P.H. Chem. Eur. J. 13 (2007) 2369
32. Dahan A., and Portnoy M. J. Am. Chem. Soc. 129 (2007) 5860
33. Kirschning A., Solodenko W., and Mennecke K. Chem. Eur. J. 12 (2006) 5972
34. Karbass N., Sans V., García-Verdugo E., and Luis M.I.BurgueteS.V. Chem. Commun. 29 (2006) 3095
35. Lozano P., García-Verdugo E., Piamtongkam R., Karbass N., De Diego T., Burguete M.I., Luis S.V., and Iborra J.L. Adv. Syn. Catal. 349 (2007) 1077
36. Burguete M.I., Erythropel H., García-Verdugo E., Luis S.V., and Sans V. Green Chem. 10 (2008) 401
37. Mehnert C.P. Chem. Eur. J. 11 (2005) 50
38. Riisager A., Fehrmann R., Haumann M., and Wasserscheid P. Eur. J. Inorg. Chem. (2006) 695
39. Gua Y., and Li G. Adv. Syn. Catal. 351 (2009) 817
40. Initial studies with metal NHC complexes based on supported imidazolium salts can be found in. Altava B., Burguete M.I., Garcia-Verdugo E., Karbass N., Luis S.V., Puzary A., and Sans V. Tetrahedron Lett. 47 (2006) 2311
41. Gil W., Boczoń K., Trzeciak A.M., Ziółkowski J.J., Garcia-Verdugo E., Luis S.V., and Sans V. J. Mol. Catal. A 309 (2009) 131-136
42. Metal nanoparticles with narrow size distributions have been synthesized in imidazolium-based ILs. The IL acts as a template for the formation of nanoscale structures and stabilizes the metal nanoparticles by the formation of "protective" anionic and cationic layers avoiding particle aggregation see Ref. [23].
43. Migowski P. J. Dupont Chem. Eur. J. 13 (2007) 32
44. Yang X., Fei Z., Zhao D., Han Ang W., Li Y., and Dyson P.J. Inorg. Chem. 47 (2008) 3292
45. Ruta M., Laurenczy G., Dyson P.J., and Kiwi-Minsker L. J. Phys. Chem. C 112 (2008) 17814
46. Redel E., Thomann R., and Janiak C. Chem. Commun. (2008) 1789
47. Altava B., Burguete M.I., García-Verdugo E., Luis S.V., and Vicent M.J. Tetrahedron 57 (2001) 8675
48. Altava B., Burguete M.I., García-Verdugo E., Luis S.V., and Vicent M.J. Tetrahedron Lett. 42 (2001) 8459
49. Galindo F., Altava B., Burguete M.I., Gavara R., and Luis S.V. J. Combin. Chem. 6 (2004) 859
50. Byun J.-W., and Lee Y.-S. Tetrahedron Lett. 45 (2004) 1837
51. Kim D.-W., and Chi D.-Y. Angew. Chem. Int. Ed. 43 (2004) 483
52. Kim J.H., Jun B.H., Byun J.W., and S Lee Y. Tetrahedron Lett. 45 (2004) 5827
53. Kim D.-W., Hong D.-J., Jang K.-S., and Chi D.-Y. Adv. Syn. Catal. 348 (2006) 1719
54. Lee D.-H., Kim J.-H., Jun B.-H., Kang H., Park J., and Lee Y.-S. Org. Lett. 10 (2008) 1609
55. Polshettiwar V., and Varma R.S. Tetrahedron 64 (2008) 4637
56. Burguete M.I., Galindo F., Garcia-Verdugo E., Karbass N., and Luis S.V. Chem. Commun. 29 (2007) 3087
57. Sommer W.J., and Werk Coor M. Chem. Rev. 251 (2007) 860
58. Kim J.H., Kim J.W., Shokouhimehr M., and Lee Y.S. J. Org. Chem. 70 (2005) 6714
59. It is worthy to mention that both materials SILLPs and palladium complex-SILLPs can be easily synthesized in grams scale under aerobic conditions being storable without any significant modifications during months.
60. Narayanan R., and El-Sayed M.A. J. Am. Chem. Soc. 125 (2003) 8340
61. Hu J., and Liu Y.B. Langmuir 21 (2005) 2121
62. Davies I.W., Matty L., Hughes D.L., and Reider P.J. J. Am. Chem. Soc. 123 (2001) 10139
63. Lipshutz B.H., Tasler S., Chrisman W., Spliethoff B., and Tesche B. J. Org. Chem. 68 (2003) 1177
64. Zhao F., Bhanage M.B., Shirai M., and Arai M. J. Mol. Catal. A 142 (1999) 383
65. Kohler K., Heidenreich R.G., Krauter J.G.E., and Pietsch M. Chem. Eur. J. 8 (2002) 622
66. Watzky M.A., and Finke R.G. J. Am. Chem. Soc. 119 (1997) 10382
67. Weddle K.S., Aiken III J.D., and Finke R.G. J. Am. Chem. Soc. 120 (1998) 5653
68. Widegren J.A., Aiken III J.D., Azkar S., and Finke R.G. Chem. Mat. 13 (2001) 312
69. Widegren J.A., Bennett M.A., and Finke R.G. J. Am. Chem. Soc. 125 (2003) 10301
70. Widegren J.A., and Finke R.G. J. Mol. Catal. A 198 (2003) 317
71. 2), in which metal species are added to a soluble nanoparticle (where A is the Pd complex and B is soluble Pd(0)). When combined with the pseudo-elementary step for the Heck reaction, B + olefin + iodoarene → B + HI + coupling product, these steps can be fit to the kinetic data (see supporting information). Ref. [35].
72. Thathagar M.B., ten Elshof J.E., and Rothenberg G. Angew. Chem. Int. Ed. 45 (2006) 2886
73. Gaikwad A.V., Holuigue A., Thathagar M.B., ten Elshof J.E., and Rothenberg G. Chem. Eur. J. 13 (2007) 6908
74. Trzeciak A.M., and Ziolkowski J.J. Coord. Chem. Rev. 251 (2007) 1281
75. Zhao F., Shirai M., Ikushima Y., and Arai M. J. Mol. Catal. A 180 (2002) 211
76. Webb J.D., MacQuarrie S., McEleney K., and Crudden C.M. J. Catal. 252 (2007) 97
77. Budroni G., Corma A., García H., and Primo A. J. Catal. 251 (2007) 345
78. Köhler K., Heidenreich R.G., Soomro S.S., and Pröckla S.S. Adv. Syn. Catal. 350 (2008) 2930
79. Mu X., Meng J., Li Z.-C., and Kou Y. J. Am. Chem. Soc. 127 (2005) 9694
80. Sheldon R.A., Wallau M., Arends I.W.C.E., and Schuchardt U. Acc. Chem. Res. 31 (1998) 485
81. Astruc D. Inorg. Chem. 46 (2007) 1884
82. Xu L., Chen W., and Xiao J. Organometallics 19 (2000) 1123
83. Herrmann W.A., Schwarz J., Gardiner M.G., and Splieger M. J. Organomet. Chem. 575 (1999) 80
84. Fehlhammer W.P., Bliss T., Kernbach U., and Brüdgam I. J. Organomet. Chem. 490 (1995) 149
85. Yaroslavsky C., Patchornik A., and Katchalski E. Tetrahedron Lett. 11 (1970) 3629
86. Alexandratos S.D., and Miller D.H.J. Macromolecules 29 (1996) 8025
87. Alexandratos S.D., and Miller D.H.J. Macromolecules 33 (2000) 2011
88. Ott L.S., and Finke R.G. Chem. Mater. 20 (2008) 2592