Characterizing ionic liquids as reaction media through a chemical probe

Chemistry - A European Journal

Volumn 13, Issue 6, 2007, Pages 1834-1841

  Dichiarante, Valentina ^a   Betti, Cecilia ^b   Fagnoni, Maurizio ^a   Maia, Angelamaria ^c   Landini, Dario ^b   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

^c CNR   (Italy)

Author keywords

C C coupling; Cations; Ionic liquids; Photochemistry; Solvent effects

Indexed keywords

DERIVATIVES; NITROGEN COMPOUNDS; POSITIVE IONS; REACTION KINETICS;

C-C COUPLING; SOLVENT EFFECTS;

IONIC LIQUIDS;

EID: 34250673435     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601078     Document Type: Article

References (57)

1. Note, however, that dialkylimidazolium cations have been revealed in the vapor phase upon heating ILs. See: H. Chen, Z. Ouyang, R. Graham Cooks, Angew. Chem. 2006, 118, 3738-3742;
2. Angew. Chem. Int. Ed. 2006, 45, 3656-3660.
3. a) Green Industrial Applications of Ionic Liquids (Eds.: R. D. Rogers, K. R. Seddon, S. Volkov), Kluwer, Dordrecht, 2003;
4. b) "Ionic liquids as Green Solvents: Progress and Prospects":ACS Symp. Ser. 2003, 856, whole volume;
5. c) T. Welton, Coord. Chem. Rev. 2004, 248, 2459-2477;
6. d) C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 2005, 18, 275-297;
7. e) N. Jain, A. Kumar, S. Chauhan, S. M. S. Chauhan, Tetrahedron 2005, 61, 1015-1060;
8. f) S. Lee, Chem. Commun. 2006, 1049-1063.
9. a) R. J. Bernot, M. A. Brueseke, M. A. Evans-White, G. A. Lamberti, Environ. Toxicol. Chem. 2005, 24, 87-92;
10. b) C. Pretti, C. Chiappe, D. Pieraccini, M. Gregori, F. Abramo, G. Monni, L. Intorre, Green Chem. 2006, 8, 238-240.
11. See for example: J. Dupont, J. Spencer, Angew. Chem. 2004, 116, 5408-5409;
12. Angew. Chem. Int. Ed. 2004, 43, 5296-5297.
13. M. J. Muldoon, A. J. McLean, C. M. Gordon, I. R. Dunkln, Chem. Commun. 2001, 2364-2365.
14. a) K. K. Laali, V.J. Gettwert, J. Fluorine Chem. 2001, 107, 31-34;
15. b) R. Bini, C. Chiappe, E. Marmugi, D. Pieraccini, Chem. Commun. 2006, 897-899.
16. a) M. Fagnoni, A. Albini, Acc. Chem. Res. 2005, 38, 713-721;
17. b) M. Fagnoni, Lett. Org. Chem. 2006, 3, 253-259.
18. V. Dichiarante, M . Fagnoni, A. Albini, Chem. Commun. 2006, 3001-3003.
19. E. Fasani, F. F. Barberis Negra, M. Mella, S. Monti, A. Albini, J. Org. Chem. 1999, 64, 5388-5395.
20. M. Freccero, M. Fagnoni, A. Albini, J. Am. Chem. Soc. 2003, 125, 13182-13190.
21. a) K. R. Seddon, A. Stark, M. J. Torres, Pure Appl. Chem. 2000, 72, 2275-2287;
22. b) M. Antonietti, D. Kuang, B. Smarsly, Y. Zhou, Angew. Chem. 2004, 116, 5096-5100;
23. Angew. Chem. Int. Ed. 2004, 43, 4988-4992.
24. During this period the salt dissolved completely.
25. Notice the formation of tetrahydropyrane 8 requires Wagner-Meerwein migration, a process previously observed in the phenyl cation addition; see reference [7b].
26. B. Guizzardi, M. Mella, M. Fagnoni, A. Albini, Tetrahedron 2000, 56, 9383-9389.
27. For related ESI-MS mass experiments on imidazolium ILs, see: F. C. Gozzo, L. S. Santos, R. Augusti, C. S. Consorti, J. Dupont, M. N. Eberlin, Chem. Eur. J. 2004, 10, 6187-6193.
28. a) M. J. Muldoon, C. M. Gordon, I. R. Dunkin, J. Chem. Soc. Perkin Trans. 2 2001, 433-435;
29. b) C. Reichardt, Green Chem. 2005, 7, 339-351;
30. c) G. Angelini, C. Chiappe, P. De Maria, A. Fontana, F. Gasparrini, D. Pieraccini, M. Pierini, G. Siani, J. Org. Chem. 2005, 70, 8193-8196;
31. d) T. Köddermann, C. Wertz, A. Heintz, R. Ludwig, Angew. Chem. 2006, 118, 3780-3785;
32. Angew. Chem. Int. Ed. 2006, 45, 3697-3702.
33. a) P. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzel, Inorg. Chem. 1996, 35, 1168-1178;
34. b) K. A. Fletcher, S. Pandey, I. K. Storey, A. E. Hendricks, S. Pandey, Anal. Chim. Acta 2002, 453, 89-96.
35. A. Mele, G. Romanò, M. Giannone, E. Ragg, G. Fronza, G. Raos, V. Marcon, Angew. Chem. 2006, 118, 1141-1144;
36. Angew. Chem. Int. Ed. 2006, 45, 1123-1126.
37. a) J. Dupont, J. Braz. Chem. Soc. 2004, 15, 341-350;
38. b) J. N. A. Canongia Lopes, A. A. H. Pádua, J. Phys. Chem. B 2006, 110, 3330-3335;
39. c) J. L. Anderson, J. Ding, T. Welton, D. W. Armstrong, J. Am. Chem. Soc. 2002, 124, 14247-14254.
40. a) X. Creary, E. D. Willis, M. Gagnon, J. Am. Chem. Soc. 2005, 127, 18114-18120;
41. b) M. C. Law, K.-Y. Wong, T. H. Chan, Chem. Commun. 2006, 2457-2459.
42. "Photochemistry in Ionic Liquids"R. M. Pagni, C. M. Gordon, in Handbook of Organic Photochemistry and Photobiology, 2nd ed. CRC , Boca Raton, 2004.
43. M. Alvaro, B. Ferrer, H. Garcia, M. Narayana, Chem. Phys. Lett. 2002, 362, 435-440.
44. Q. Yang, D. D. Dionysiou, J. Photochem. Photobiol. A 2004, 165, 229-240.
45. II complex to form bis(methylimidazole) dichloropalladate. See: J. E. L. Dullius, P. A. Z. Suarez, S. Einloft, R. F. de Souza, J. Dupont, Organometallics 1998, 17, 815-819.
46. It has been proposed that benzene and arenes were staggered through π-π sandwich interactions between two bmim cations; see reference [19a].
47. D. J. Moody, N. A. Hamill (Avecia Pharmaceuticals), WO 2004108633, 2004.
48. 1 of the singlet, as formed, for example, from the photolysis of phenyl diazonium salts.
49. M. De Carolis, S. Protti, M. Fagnoni, A. Albini, Angew. Chem. 2005, 117, 1258-1262;
50. Angew. Chem. Int. Ed. 2005, 44, 1232-1236.
51. a) L. Cammarata, S. G. Kazarian, P. A. Salter, T. Welton, Phys. Chem. Chem. Phys. 2001, 3, 5192-5200;
52. b) D. Landini, A. Maia, Tetrahedron Lett. 2005, 46, 3961-3963.
53. L. Cammarata, S. G. Kazarian, P. A. Salter, T. Welton, Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.
54. D. L. Astolfi, F. C. Mayville, Jr., Tetrahedron Lett. 2003, 44, 9223-9224.
55. H. R. Williams, H. S. Mosher, J. Am. Chem. Soc. 1954, 76, 2984-2990.
56. C. W. Y. Chung, P. H. Toy, Tetrahedron 2005, 61, 709-715.
57. The yield of tetrahydrofurans or -pyrans of structures 7 and 8 from the irradiation of 1 or other chloroaromatics dramatically depends on the solvent used. This topic is currently under investigation.