Pyridine-bridged benzimidazolium salts: Synthesis, aggregation, and application as phase-transfer catalysts

Angewandte Chemie - International Edition

Volumn 47, Issue 37, 2008, Pages 7127-7131

  Tu, Tao ^a   Assenmacher, Wilfried ^a   Peterlik, Herwig ^b   Schnakenburg, Gregor ^a   Dötz, Karl Heinz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

Aggregation; Benzimidazolium salts; Gels; Phase transfer catalysis; Self assembly

Indexed keywords

EID: 54749113602     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801628     Document Type: Article

References (54)

1. R. J. Sundberg, R. B. Martin, Chem. Rev. 1974, 74, 471.
2. a) W. Huang, S. Zhang, L. Dai, Y. Shan, J. Chem. Res. 2004, 506;
3. b) F. Wang, Z. Chen, Q. Zheng, J. Chem. Res. 2004, 206;
4. for imidazolium salts as ionic liquids, see: c) S. Lee, Chem. Commun. 2006, 1049
5. and d) P. Wasserscheid, T. Welton, Ionic liquids in Synthesis, 2nd ed., Wiley-VCH, Weinheim, 2007.
6. a) F. E. Hahn, M. C. Jahnke, T. Pape, Organometallics 2007, 26, 150;
7. b) F. E. Hahn, M. C. Jahnke, T. Pape, Organometallics 2006, 25, 5927;
8. c) F. E. Hahn, M. C. Jahnke, V. Gomez-Benitez, D. Morales-Morales, T. Pape, Organometallics 2005, 24, 6458;
9. d) F. E. Hahn, M. Foth, J. Organomet. Chem. 1999, 585, 241;
10. e) F. E. Hahn, L. Wittenbecher, R. Boese, D. Blaser, Chem. Eur. J. 1999, 5, 1931.
11. a) I. J. B. Lin, C. S. Vasam, Coord. Chem. Rev. 2007, 251, 642, and references therein;
12. b) S. P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, Weinheim, 2006;
13. c) F. E. Hahn, Angew. Chem. 2006, 118, 1374;
14. Angew. Chem. Int. Ed. 2006, 45, 1348;
15. d) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
16. Angew. Chem. Int. Ed. 2002, 41, 1290.
17. a) P. Terech, R. G. Weiss, Molecular Gels: Materials with Self-Assembled Fibrillar Networks, Springer, Dordrecht, 2006;
18. b) M. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489;
19. c) D. J. Abdallah, R. G. Weiss, Adv. Mater. 2000, 12, 1237;
20. d) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133.
21. a) Low-Molecular-Weight Organic Gelators: Tetrahedron 2007, 63, 7271;
22. b) Low-Molecular-Mass Gelators: F. Fages, F. Vögtle, M. Žinić, Top. Curr. Chem. 2005, 256;
23. c) N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821;
24. d) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. Schenning, Chem. Rev. 2005, 105, 1491;
25. e) L. A. Estroff, A. D. Hamilton, Chem. Rev. 2004, 104, 1201.
26. a) T. Tu, W. Assenmacher, H. Peterlik, R. Weisbarth, M. Nieger, K. H. Dötz, Angew. Chem. 2007, 119, 6486;
27. Angew. Chem. Int. Ed. 2007, 46, 6368;
28. b) T. Klawonn, A. Gansäuer, I. Winkler, T. Lauterbach, D. Franke, R. J. M. Nolte, M. C. Feiters, H. Börner, J. Hentschel, K. H. Dötz, Chem. Commun. 2007, 1894;
29. c) G. Bühler, M. C. Feiters, R. J. M. Nolte, K. H. Dötz, Angew. Chem. 2003, 115, 2599;
30. Angew. Chem. Int. Ed. 2003, 42, 2494.
31. See the Supporting Information.
32. A. Takahashi, M. Sakai, T. Kato, Polym. J. 1980, 12, 335.
33. a) O. Lebel, M. Perron, T. Maris, S. F. Zalzal, A. Nanci, J. D. Wuest, Chem. Mater. 2006, 18, 3616;
34. b) D. R. Trivedi, P. Dastidar, Chem. Mater. 2006, 18, 1470;
35. c) D. R. Trivedi, P. Dastidar, Cryst. Growth Des. 2006, 6, 2114;
36. d) D. K. Kumar, D. A. Jose, A. Das, P. Dastidar, Chem. Commun. 2005, 4059;
37. e) J. Makarević, M. Jokić, Z. Raza, Z. Š tefanić, B. Kojić-Prodić, M. Žinić, Chem. Eur. J. 2003, 9, 5567.
38. a) P. Terech, F. Volino, R. Ramasseul, J. Phys. 1985, 46, 895;
39. b) O. Glatter, O. Kratky, Small-Angle X-ray Scattering, Academic Press, London, 1982.
40. F. Fages, Angew. Chem. 2006, 118, 1710;
41. Angew. Chem. Int. Ed. 2006, 45, 1680.
42. a) B. Xing, M.-F. Choi, B. Xu, Chem. Eur. J. 2002, 8, 5028;
43. b) J. F. Miravet, B. Escuder, Chem. Commun. 2005, 5796.
44. a) T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300;
45. Angew. Chem. Int. Ed. 2007, 46, 4222;
46. b) M. J. O'Donell, Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000;
47. c) T. Shioiri, S. Arai, Stimulating Concepts in Chemistry (Eds.: F. Vögtle, F. Stoddart, M. Shibasaki), Wiley, New York, 2000;
48. d) A. Nelson, Angew. Chem. 1999, 111, 1685;
49. Angew. Chem. Int. Ed. 1999, 38, 1583.
50. a) A. Melaiye, Z. Sun, K. Hindi, A. Milsted, D. Ely, D. H. Reneker, C. A. Tessier, W. J. Youngs, J. Am. Chem. Soc. 2005, 127, 2285;
51. b) A. A. Danopoulos, A. A. D. Tulloch, S. Winston, G. Eastham, M. B. Hursthous, Dalton Trans. 2003, 1009.
52. a) P. Rajakumar, M. Dhanasekaran, Synthesis 2006, 654;
53. b) M. V. Baker, M. J. Bosnich, D. H. Brown, L. T. Byrne, V. J. Hesler, B. W. Skelton, A. H. White, C. C. Williams, J. Org. Chem. 2004, 69, 7640;
54. c) P. Rajakumar, M. Dhanasekaran, Tetrahedron 2002, 58, 1355.