Nitrile-functionalized pyridinium ionic liquids: Synthesis, characterization, and their application in carbon-carbon coupling reactions

Journal of the American Chemical Society

Volumn 126, Issue 48, 2004, Pages 15876-15882

  Zhao, Dongbin ^a   Fei, Zhaofu ^a   Geldbach, Tilmann J ^a   Scopelliti, Rosario ^a   Dyson, Paul J ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; POSITIVE IONS; SINGLE CRYSTALS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION ANALYSIS;

COUPLING REACTIONS; IONIC LIQUIDS; NITRILE MOIETY;

NITRILE RESINS;

ANION; CARBON; N BUTYRONITRILE PYRIDINIUM; NANOPARTICLE; PALLADIUM; PALLADIUM CHLORIDE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC EMISSION SPECTROMETRY; CATALYSIS; CATALYST; LEACHING; LIQUID; SOLID STATE; STILLE REACTION; SUZUKI REACTION; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

EID: 10044231966     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0463482     Document Type: Article

References (74)

1. Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351.
2. (b) Welton, T. Chem. Rev. 1999, 99, 2071.
3. (c) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
4. (d) Gordon, C. M. Appl. Catal., A 2001, 222, 101.
5. (e) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A 2002, 182-183, 419.
6. (f) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157.
7. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
8. (h) Song, C. E. Chem. Commun. 2004, 1033.
9. Cornils, B. Org. Process Res. Dev. 1998, 2, 121.
10. Maitlis, P. M.; Long, H. C; Quyoum, R.; Turner, M. L.; Wang, Z. Q. Chem. Commun. 1996, 1.
11. For examples, see: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25. (c) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149. (d) Wasserscheid, P.; Gordon, C. M.; Hilgers. C.; Muldoon, M. J.; Dunkin, I. R. Chem. Commun. 2001, 1186. (e) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (f) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705.
12. For examples, see: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25. (c) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149. (d) Wasserscheid, P.; Gordon, C. M.; Hilgers. C.; Muldoon, M. J.; Dunkin, I. R. Chem. Commun. 2001, 1186. (e) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (f) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705.
13. For examples, see: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25. (c) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149. (d) Wasserscheid, P.; Gordon, C. M.; Hilgers. C.; Muldoon, M. J.; Dunkin, I. R. Chem. Commun. 2001, 1186. (e) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (f) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705.
14. For examples, see: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25. (c) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149. (d) Wasserscheid, P.; Gordon, C. M.; Hilgers. C.; Muldoon, M. J.; Dunkin, I. R. Chem. Commun. 2001, 1186. (e) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (f) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705.
15. For examples, see: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25. (c) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149. (d) Wasserscheid, P.; Gordon, C. M.; Hilgers. C.; Muldoon, M. J.; Dunkin, I. R. Chem. Commun. 2001, 1186. (e) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (f) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705.
16. For examples, see: (a) Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25. (c) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149. (d) Wasserscheid, P.; Gordon, C. M.; Hilgers. C.; Muldoon, M. J.; Dunkin, I. R. Chem. Commun. 2001, 1186. (e) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (f) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705.
17. For examples, see: (a) Favre, F.; Olivier-Bourbigou, H.; Commereuc, D.; Saussine, L. Chem. Commun. 2001, 1360. (b) Wasserscheid, P.; Waffenschmidt, H.; Machnizti, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. (c) Braucer, D. J.; Kottsieper, K. W.; Liek, C.; Stelzer, O.; Waffenschmidt, H.; Wasserscheid, P. J. Organomet. Chem. 2001, 630, 177. (d) Kottsieper, K. W.; Stelzer, O.; Wasserscheid, P. J. Mol. Catal. A 2001, 175, 285. (e) Brasse, C. C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P. Organometallics 2000, 19, 3818.
18. For examples, see: (a) Favre, F.; Olivier-Bourbigou, H.; Commereuc, D.; Saussine, L. Chem. Commun. 2001, 1360. (b) Wasserscheid, P.; Waffenschmidt, H.; Machnizti, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. (c) Braucer, D. J.; Kottsieper, K. W.; Liek, C.; Stelzer, O.; Waffenschmidt, H.; Wasserscheid, P. J. Organomet. Chem. 2001, 630, 177. (d) Kottsieper, K. W.; Stelzer, O.; Wasserscheid, P. J. Mol. Catal. A 2001, 175, 285. (e) Brasse, C. C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P. Organometallics 2000, 19, 3818.
19. For examples, see: (a) Favre, F.; Olivier-Bourbigou, H.; Commereuc, D.; Saussine, L. Chem. Commun. 2001, 1360. (b) Wasserscheid, P.; Waffenschmidt, H.; Machnizti, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. (c) Braucer, D. J.; Kottsieper, K. W.; Liek, C.; Stelzer, O.; Waffenschmidt, H.; Wasserscheid, P. J. Organomet. Chem. 2001, 630, 177. (d) Kottsieper, K. W.; Stelzer, O.; Wasserscheid, P. J. Mol. Catal. A 2001, 175, 285. (e) Brasse, C. C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P. Organometallics 2000, 19, 3818.
20. For examples, see: (a) Favre, F.; Olivier-Bourbigou, H.; Commereuc, D.; Saussine, L. Chem. Commun. 2001, 1360. (b) Wasserscheid, P.; Waffenschmidt, H.; Machnizti, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. (c) Braucer, D. J.; Kottsieper, K. W.; Liek, C.; Stelzer, O.; Waffenschmidt, H.; Wasserscheid, P. J. Organomet. Chem. 2001, 630, 177. (d) Kottsieper, K. W.; Stelzer, O.; Wasserscheid, P. J. Mol. Catal. A 2001, 175, 285. (e) Brasse, C. C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P. Organometallics 2000, 19, 3818.
21. For examples, see: (a) Favre, F.; Olivier-Bourbigou, H.; Commereuc, D.; Saussine, L. Chem. Commun. 2001, 1360. (b) Wasserscheid, P.; Waffenschmidt, H.; Machnizti, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. (c) Braucer, D. J.; Kottsieper, K. W.; Liek, C.; Stelzer, O.; Waffenschmidt, H.; Wasserscheid, P. J. Organomet. Chem. 2001, 630, 177. (d) Kottsieper, K. W.; Stelzer, O.; Wasserscheid, P. J. Mol. Catal. A 2001, 175, 285. (e) Brasse, C. C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P. Organometallics 2000, 19, 3818.
22. Zhao, D.; Fei, Z.; Scopelliti, R.; Dyson, P. J. Inorg. Chem. 2004, 43, 2197.
23. Herrmann, W. A.; Köcher, C.; Goossen, L. J.; Artus, G. R. J. Chem.-Eur. J. 1996, 2, 1627.
24. Lee, K.-M.; Lee, Y.-T.-Y.; Lin, J. B. J. Mater. Chem. 2003, 13, 1079.
25. Branco, L. C.; Rosa, J. N.; Moura Ramos, J. J.; Alfons, C. A. M. Chem.-Eur. J. 2002, 8, 3671.
26. Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H., Jr. J. Am. Chem. Soc. 2002, 124, 5962.
27. (b) Holbrey, J. D.; Reichert, W. M.; Tkatchenko, I.; Bouajila, E.; Walter, O.; Tommasi, I. Chem. Commun. 2003, 28.
28. Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H., Jr.; Rogers, R. D. Chem. Commun. 2001, 135.
29. Merrigan, T. L.; Bates, E. D.; Dorman, S. C.; Davis, J. H., Jr. Chem. Commun. 2000, 2051.
30. Klingelhöfer, S.; Heitz, W.; Greiner, A.; Oestreich, S.; Förster, S.; Antonietti, M. J. Am. Chem. Soc. 1997, 119, 10116.
31. (b) Huana, J.; Jiang, T.; Han, B.; Gao, H.; Chans, Y.; Zhao, G.; Wu, W. Chem. Commun. 2003, 1654.
32. Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P. J. Am. Chem. Soc. 2002, 124, 4228.
33. Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixeira, S. R.; Dupont, J. Chem-Eur. J. 2003, 3264.
34. Scheeren, C. W.; Machado, G.; Dupont, J.; Fichtner, P. F. P.; Texeira, S. R. Inorg. Chem. 2003, 42, 4738.
35. Kim, K.-S.; Demberelnyamba, D.; Lee, H. Langmuir 2004, 20, 556.
36. (b) Itoh, H.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 2004, 126, 3026.
37. Kumar, A.; Pawar, S. S. J. Mol. Catal. A 2004, 208, 33.
38. Zhu, Y.; Carpenter, K.; Bun, C. C.; Bahnmueller, S.; Ke, C. P.; Srid, V. S.; Kee, L. W.; Hawthorne, M. F. Angew. Chem., Int. Ed. 2003, 42, 3792.
39. Hamill, N. A.; Hardacre, C.; McMath, S. E. J. Green Chem. 2002, 4, 139.
40. Baker, S. N.; Baker, G. A.; Kane, M. A.; Bright, F. V. J. Phys. Chem. B. 2001, 105, 9663.
41. Paradies, H. H.; Habben, F. Acta Crystallogr. 1993, C49, 744.
42. (b) Ward, D. L.; Rhinebarger, R. R.; Popov, A. I. Acta Crystallogr. 1986, C42, 1771.
43. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
44. Neve, F.; Crispini, A.; Armentano, S.; Francescangeli, O. Chem. Mater. 1998, 10, 1904.
45. (b) Neve, F.; Crispini, A. Cryst. Growth Des. 2001, 1, 387.
46. Prout, C. K.; Murray-Rust, P. J. Chem. Soc. A. 1969, 1520.
47. Kratochvil, B.; Ondracek, J.; Velisek, J.; Hasek, J. Acta Crystallogr. 1988, C44, 1579.
48. (b) Holbrey, J. D.; Reichert, W. M.; Tkatchenko, I.; Bouajila, E.; Walter, O.; Tommasi, I.; Rogers, R. D. Chem. Commun, 2003, 28.
49. (c) Golding, J. J.; MacFarlaine, D. R.; Spiccia, L.; Forsyth, M.; Skelton, B. W.; White, A. H. Chem. Commun. 1998, 1593.
50. (d) Hitchcock, P. B.; Seddon, K. R.; Welton, T. J. Chem. Soc., Dalton Trans. 1993, 2639.
51. Tsuji, J. Palladium Reagents & Catalysts: Innovations in Organic Syntheses, 2nd ed.; John Wiley and Sons Ltd.; Chichester, U.K., 2004.
52. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
53. (c) Stille, K. J. Angew. Chem., Im. Ed. 1986, 23, 508.
54. Navarro, J.; Sagi, M.; Sola. E.; Lahoz, F. J.; Dobrinovitch, I. T.; Katho, A.; Joo, F.; Oro, L. A. Adv. Synth. Catal. 2003, 345, 280.
55. (b) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem., Int. Ed. 2002, 41, 4500.
56. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058.
57. Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249.
58. (b) Mathews, C. J.; Smith, P. J.; Welton, T. J. Mol. Catal. A. 2004, 214, 27.
59. McNulty, J.; Capretta, A.; Wilson, J.; Dyck, J.; Adjabeng, G.; Robertson, A. Chem. Commun. 2002, 1986.
60. (b) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
61. (c) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616.
62. Chiappe, C.; Imperato, G.; Napolitano, E.; Pieraccini, D. Green Chem. 2004, 6, 33.
63. (b) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233.
64. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
65. Xu, L. J.; Chen, W. P.; Xiao, J. L. Organometallics 2000, 19, 1123.
66. (b) Mclachlan, F.; Mathews, C. J.; Smith, P. J.; Welton, T. Organometallics 2003, 22, 5350.
67. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
68. Bucher, S.; Hormes, J.; Modrow, H.; Brinkmann, R.; Waldöfner, N.; Bönnemann, H.; Beuermann, L.; Krischok, S.; Maus-Friedrichs, W.; Kempter, V. Surf. Sci. 2002, 497, 321.
69. Dyson, P. J.; McIndoe, J. S. Inorg. Chim. Acta 2003, 354, 68.
70. Oxford Diffraction Ltd., 68 Milton Park, Abingdon, OX14 4 RX, U.K., 2003.
71. Sheldrick, G. M. SHELX-97: Structure Solution and Refinement Package; University of Göttingen: Göttingen, Germany, 1997.
72. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
73. Walker, N.; Stuart, D. Acta Crystallogr. 1983, A39, 158.
74. Beary, E. S.; Paulsen, P. J. Anal. Chem. 1995, 67, 3193.