Carbon-centered strong bases in phosphonium ionic liquids

Journal of Organic Chemistry

Volumn 73, Issue 3, 2008, Pages 801-812

  Ramnial, Taramatee ^a   Taylor, Stephanie A ^a   Bender, Marissa L ^b   Gorodetsky, Brian ^a   Lee, Peter T K ^b   Dickie, Diane A ^a   McCollum, Brett M ^a   Pye, Cory C ^b   Walsby, Charles J ^a   Clyburne, Jason A C ^b  

^a SIMON FRASER UNIVERSITY   (Canada)

^b SAINT MARY S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIN CONDENSATION; TETRAALKYLPHOSPHONIUM IONS;

CARBON; DEUTERIUM; ELECTROCHEMISTRY; PARAMAGNETIC RESONANCE;

IONIC LIQUIDS;

ANION; CARBENOID; CARBON; DEUTERIUM; GRIGNARD REAGENT; HYDROXIDE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; ISOCYANATE; ORGANIC COMPOUND; PHOSPHONIUM DERIVATIVE; PHOSPHORANE DERIVATIVE; SOLVENT; TETRADECYL (TRIHEXYL)PHOSPHONIUM DECANOATE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CROSS COUPLING REACTION; DECOMPOSITION; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ISOTOPE LABELING; POLYMERIZATION; REACTION ANALYSIS; REDUCTION;

EID: 38849178824     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701289d     Document Type: Article

References (81)

1. Williamson, P. T.; Anastas, C. T. Green Chemistry: Designing Chemistry for the Environment; ACS Symp. Ser. No. 626; American Chemical Society: Washington, DC, 1996.
2. Rogers, R. D.; Seddon, K. R. Ionic Liquids: Industrial Applications to Green Chemistry; American Chemical Society: Washington, DC, 2002.
3. Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157.
4. Ren, X. R.; Brenner, A.; Wu, J. X.; Ou, W. Proc. Electrochem. Soc. 2002, 2002 (19), 165.
5. Freemantle, M. Chem. Eng. News 2004, 82 (45), 44.
6. Lancaster, M. Green Chemistry: An Introductory Text; Royal Society of Chemistry: Cambridge, UK, 2002.
7. Wilkes, J. S. Green Chem. 2002, 4, 73.
8. (a) It should be noted that under specific conditions, some ILs are, in fact, combustible. However, the bulk properties of an IL are dramatically different than, for example, fine mists which in many ways are comparable to normal solvent vapors.
9. (b) Smiglak, M.; Reichert, W. M.; Holbrey, J. D.; Wilkes, J. S.; Sun, L.; Thrasher, J. S.; Kirichenko, K.; Singh, S.; Katritzky, A. R.; Rogers, R. D. Chem. Commun. 2006, 2554.
10. Welton, T. Chem. Rev. 1999, 99, 2071.
11. Tempel, Daniel Joseph Henderson Philip Bruce Brzozowski, Jeffrey Richard Pearlstein, Ronald Martin, U.S. Patent 2006060817, 2006.
12. +. In ILs, such reactions can also occur, but these lead to decomposition and contamination of the IL. We recognize, however, that these decompositions can often result in the formation of the truly active species in select reactions.
13. (a) There have been numerous reports dealing with the hydrolysis of anions, particularly tetrafluoroborate and hexafluorophosphate. These reactions do cause significant problems and perhaps most important is the evolution of HF which can damage glass and metal.
14. (b) Scammells, P. J.; Scott, J. L.; Singer, R. D. Aust. J. Chem. 2005, 58, 155.
15. Qiao, K.; Yokoyama, C. Chem. Lett. 2004, 33, 472.
16. Stark, A.; MacLean, B. L.; Singer, R. D. J. Chem. Soc., Dalton Trans. 1999, 63.
17. 3 which is a good Lewis acid for catalysis. We use the term "acidic" to emphasize the high reactivity of the C-H fragment in ImILs, which, with strong bases, behave as protic acids.
18. (b) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223.
19. (c) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391.
20. Freemantle, M. Chem. Eng. News 2005, 83 (33), 31.
21. Aggarwal, V. K.; Emme, I.; Mereu, A. Chem. Commun. 2002, 1612.
22. Dupont, J.; Spencer, J. Angew. Chem., Int. Ed. 2004, 43, 5296.
23. See, for example: Chowdhury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363.
24. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
25. Ott, L. S.; Cline, M. L.; Deetlefs, M.; Seddon, K. R.; Finke, R. G. J. Am. Chem. Soc. 2005, 127, 5758.
26. Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
27. Arduengo, A. J., III Acc. Chem. Res. 1999, 32, 913.
28. Cowley, A. H. J. Organomet. Chem. 2001, 617, 105.
29. Herrmann, W. A.; Öfele, K.; Elison, M.; Kühn, F. E.; Roesky, P. W. J. Organomet. Chem. 1994, 480, C7.
30. Abernethy, C. D.; Codd, G. M.; Spicer, M. D.; Taylor, M. K. J. Am. Chem. Soc. 2003, 125, 1128.
31. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
32. Schottenberger, H.; Wurst, K.; Horvath, U. E. I.; Cronje, S.; Lukasser, J.; Polin, J.; McKenzie, J. M.; Raubenheimer, H. G. Dalton. Trans. 2003, 4275.
33. Gordon, C. M.; McCluskey, A. Chem. Commun. 1999, 1431.
34. Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124.
35. Kitazume, T.; Kasai, K. Green Chem. 2001, 3, 30.
36. Law, M. C.; Wong, K-Y.; Chan, T. H. Green Chem. 2004, 6, 241.
37. Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123.
38. Mathews, C. J.; Smith, P. J.; Welton, T.; White, A. J. P.; Williams, D. J. Organometallics 2001, 20, 3848.
39. Hasan, M.; Kazhevnikov, I. V.; Rafiq, M.; Siddiqui, H.; Femoni, C.; Steiner, A.; Winterton, N. Inorg. Chem. 2001, 40, 795.
40. Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733.
41. Córdoba, R.; Plumet, J. Tetrahedron Lett. 2003, 44, 6157.
42. Law, M. C.; Wong, K. W.; Chan, T. H. Chem. Commun. 2006, 2457.
43. Handy, S. T. J. Org. Chem. 2006, 71, 4659.
44. Vaclav, J.; Wilhelm, R. Green Chem. 2005, 7, 844.
45. Kim, Y. J.; Varma, R. S. J. Org. Chem. 2005, 7882.
46. Bradaric, C. J.; Downard, A.; Kennedy, C.; Robertson, A. J.; Zhou, Y. Green Chem. 2003, 5, 143.
47. McNulty, J.; Capretta, A.; Cheekoori, S.; Clyburne, J. A. C.; Robertson, A. J. Chim. Oggi Chem. Today 2004, 22, 13.
48. Ramnial, T.; Ino, D. D.; Clyburne, J. A. C. Chem. Commun. 2005, 325.
49. Ramnial, T.; Hauser, M. K.; Clyburne, J. A. C. Aust. J. Chem. 2006, 59, 298.
50. Gorodetsky, B.; Ramnial, T.; Branda, N. R.; Clyburne, J. A. C. Chem. Commun. 2004, 1972.
51. Maruyama, K.; Katagiri, T. J. Am. Chem. Soc. 1986, 108, 6263.
52. Jurèík, V.; Wilhelm, R. Green Chem. 2005, 7, 844.
53. Birbilis, N.; Howlett, P. C.; MacFarlane, D. R.; Forsyth, M. Surf. Coat. Technol. 2007, 201, 4496.
54. Elschenbroich, C.; Salzer, A. Organometallics: A Concise Introduction; VCH: Weinheim, Germany, 1992.
55. Ramnial, T.; Taylor, S. A.; Clyburne, J. A. C.; Walsby, C. J. Chem. Commun. 2007, 2066.
56. Krasovskiy, A.; Straub, B. F.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 159.
57. Alder, R. W.; Allen, P. R.; Williams, S. J. J. Chem. Soc., Chem. Commun. 1995, 1267.
58. Kim, Y.-J.; Streitwieser, A. J. Am. Chem. Soc. 2002, 124, 5757.
59. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
60. Carmalt, C. J.; Cowley, A. H. Adv. Inorg. Chem. 2000, 50, 1.
61. Arduengo, A. J., III; Calabrese, J. C.; Cowley, A. H.; Rasika Dias, H. V.; Goerlich, J. R.; Marshall, W. J.; Riegel, B. Inorg. Chem. 1997, 36, 2151.
62. Böhm, V. P. W.; Gstöttmaryr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387.
63. Terao, J.; Ikumi, A.; Kuniyasu, H.; Kanbe, N. J. Am. Chem. Soc. 2003, 125, 5646.
64. Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions, Mechanism, and Structure; John Wiley & Sons, Inc.: New York, 2001.
65. For chemistry of stabilized Wittig reagents in ILs see: Le Boulaire, V.; Gree, R. Chem. Commun 2000, 2195-2196.
66. Schmidbaur, H.; Buchner, W.; Scheutzow, D. Chem. Ber. 1973, 106, 1251.
67. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 11, 1091.
68. Gerritsma, D. A.; Robertson, A.; McNulty, J.; Capretta, A. Tetrahedron Lett. 2004, 45, 7629.
69. de Bellefon, C.; Pollet, E.; Grenuillet, P. J. Mol. Catal. A: Chem. 1999, 145, 121.
70. Landini, D.; Maia, A.; Montanari, F. J. Chem. Soc., Chem. Commun. 1977, 4, 112.
71. McNulty, J.; Dyck, J.; Larichev, V.; Capretta, A.; Roberston, A. J. Lett. Org. Chem. 2004, 1, 137.
72. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, S.; Mason, S. A. New J. Chem. 2000, 24, 477.
73. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
74. Albright, T. A.; Gordon, M. D.; Freeman, W. J.; Schweizer, E. E. J. Am. Chem. Soc. 1976, 98, 6249.
75. Brooks, C. A.; Doherty, A. P. J. Phys. Chem. B 2005, 109, 6276.
76. Buzzeo, M. C.; Evans, R. G.; Compton, R. G. ChemPhysChem 2004, 5, 1106.
77. McKenzie, I.; Brodovitch, J.-C.; Percival, P. W.; Ramnial, T.; Clyburne, J. A. C. J. Am. Chem. Soc. 2003, 125, 11565.
78. Behar, D.; Gonzalez, C.; Neta, P. J. Phys. Chem. A 2001, 105, 7607.
79. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55, 14523.
80. Öfele, K.; Herrmann, W. A.; Mihalios, D.; Elison, M.; Herdtweck, E.; Scherer, W.; Mink, J. J. Organomet. Chem. 1993, 459, 177.
81. Frisch, M. J.; Tracks, G. W.; Schlegel, H. B.; Scuseria, G. B.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 2002.