Triazatriangulenium cations: Highly stable carbocations for phase-transfer catalysis

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4343-4346

  Nicolas, Cyril ^a   Lacour, Jérôme ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749004775     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0617392     Document Type: Article

References (69)

1. Makosza, M.; Serafin, B. Rocz. Chem. 1965, 39, 1223-1230.
2. Makosza, M.; Jonczyk, A. Org. Synth. 1976, 55, 91-95.
3. Starks, C. M.; Liotta, C. Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York, 1978.
4. Starks, C. M., Liotta, C. L., Halpern, M., Eds.; Phase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives; Springer: New York, 1994.
5. Makosza, M.; Fedorynski, M. Pol. J. Chem. 1996, 70, 1093-1110.
6. Makosza, M.; Fedorynski, M. In Handbook of Phase Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; Blackie Academic and Professional: 1997; pp 135-167.
7. Tavener, S.; Clark, J. H. Chem. Ind. (London) 1997, 22-24.
8. Wolff, M. O.; Alexander, K. M.; Belder, G. Chim. Oggi 2000, 18, 29-32.
9. Sasson, Y.; Rothenberg, G. In Handbook of Green Chemistry and Technology; Clark, J., Macquarrie, D., Eds.; Blackwell Science Ltd.: Oxford, 2002; pp 206-257.
10. Lucchese, A. M.; Marzorati, L. Quim. Nova 2000, 23, 641-652.
11. O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 727-755.
12. Makosza, M.; Fedorynski, M. In Interfacial Catalysis; Volkov, A. G., Ed.; Dekker: New York, 2003; pp 159-201.
13. Jwo, J.-J. In Interfacial Catalysis; Volkov, A. G., Ed.; Dekker: New York, 2003; pp 227-284.
14. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
15. Yadav, G. D. Top. Catal. 2004, 29, 145-161.
16. Yadav, G. D.; Lande, S. V. Adv. Synth. Catal. 2005, 347, 1235-1241.
17. Yadav, G. D.; Desai, N. M. Org. Process. Res. Dev. 2005, 9, 749-756.
18. Duxbury, D. F. Chem. Rev. 1993, 93, 381-433.
19. Olah, G. A. Angew. Chem. 1973, 85, 183-225.
20. Olah, G. A. Acc. Chem. Res. 1976, 9, 41-52.
21. Arnett, E. M.; Hofelich, T. C. J. Am. Chem. Soc. 1983, 105, 2889-2895.
22. Prakash, G. K. S.; Rawdah, T. N.; Olah, G. A. Angew. Chem. 1983, 95, 356-367.
23. Bagno, A.; Scorrano, G.; More O'Ferrall, R. A. Rev. Chem. Intermed. 1987, 7, 313-352.
24. Grützmacher, H.; Marchand, C. M. Coord. Chem. Rev. 1997, 163, 2287-344.
25. Corma, A.; Garcia, H. Top. Catal. 1998, 6, 127-140.
26. Olah, G. A. J. Org. Chem. 2001, 66, 5943-5957.
27. Richard, J. P.; Amyes, T. L.; Toteva, M. M. Acc. Chem. Res. 2001, 34, 981-988.
28. Abboud, J.-L. M.; Alkorta, I.; Davalos, J. Z.; Muller, P.; Quintanilla, E. Adv. Phys. Org. Chem. 2002, 37, 57-135.
29. Balasubramanian, M. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier Ltd.: Oxford, 2005; Vol. 6, pp 713-727.
30. Komatsu, K.; Akamatsu, H.; Jinbu, Y.; Okamoto, K. J. Am. Chem. Soc. 1988, 110, 633-634.
31. Ito, S.; Morita, N.; Asao, T. Tetrahedron Lett. 1994, 35, 751-754.
32. Ito, S.; Kikuchi, S.; Morita, N.; Asao, T. Chem. Lett. 1996, 175-176.
33. (a) Laursen, B. W.; Krebs, F. C.; Nielsen, M. F.; Bechgaard, K.; Christensen, J. B.; Harrit, N. J. Am. Chem. Soc. 1998, 120, 12255-12263.
34. (b) Laursen, B. W.; Krebs, F. C.; Nielsen, M. F.; Bechgaard, K.; Christensen, J. B.; Harrit, N. J. Am. Chem. Soc. 1999, 121, 4728.
35. (c) Laursen, B. W.; Krebs, F. C. Angew. Chem., Int. Ed. 2000, 39, 3432-3434.
36. (d) Laursen, B. W.; Krebs, F. C. Chem. - Eur. J. 2001, 7, 1773-1783.
37. Triazatriangulenium cations are related to the historically important class of trioxatriangulene derivatives. For references on these moieties and on azadioxa and diazaoxo derivatives as well, see: Martin, J. C.; Smith, R. G. J. Am. Chem. Soc. 1964, 86, 2252-2256.
38. Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790.
39. Lofthagen, M.; Siegel, J. S. J. Org. Chem. 1995, 60, 2885-2890.
40. Andresen, T. L.; Krebs, F. C.; Larsen, M.; Thorup, N. Acta Chem. Scand. 1999, 53, 410-416.
41. Krebs, F. C. Tetrahedron Lett. 2002, 44, 17-21.
42. Krebs, F. C.; Spanggaard, H.; Rozlosnik, N.; Larsen, N. B.; Jorgensen, M. Langmuir 2003, 19, 7873-7880.
43. NAr) of all six methoxy substituents of 1 by nitrogen-containing moieties; see refs 8c and 8d.
44. Fuji, K. Chem. Soc. Rev. 1993, 93, 2037-2066.
45. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 389-401.
46. Shibasaki, M.; Vogl, E. M. Organomet. Chem. 1999, 576, 1-15.
47. Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
48. Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690.
49. Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
50. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-5367.
51. Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943-11948.
52. Trost, B. M.; Jiang, C. Synthesis 2006, 369-396 and references therein.
53. 3 might be the result of a side reaction, that is, the attack of the solvent by the hydroxyde anion associated with the carbenium ion 2.
54. Ye, J.; Wang, Y.; Liu, R.; Zhang, G.; Zhang, Q.; Chen, J.; Liang, X. Chem. Commun. 2003, 2714-2715.
55. Ye, J.; Wang, Y.; Chen, J.; Liang, X. Adv. Synth. Catal. 2004, 346, 691-696 and references therein.
56. Jew, S.-S.; Lee, J.-H.; Jeong, B.-S.; Yoo, M.-S.; Kim, M.-J.; Lee, Y.-J.; Lee, J.; Choi, S.-H.; Lee, K.; Lah, M. S.; Park, H.-G. Angew. Chem., Int. Ed. 2005, 44, 1383-1385.
57. PTC conditions are particularly important for this reaction for historical and synthetic perspectives: Makosza, M.; Serafin, B.; Gajos, I. Rocz. Chem. 1969, 43, 671-676.
58. Makosza, M.; Wawrzyniewicz, M. Tetrahedron Lett. 1969, 4659-4662.
59. Makosza, M. Pure Appl. Chem. 1975, 43, 439-462.
60. Banwell, M. G.; Reum, M. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Inc.: Connecticut, 1991; Vol. 1, pp 19-64.
61. Nomura, E.; Taniguchi, H.; Otsuji, Y. Bull. Chem. Soc. Jpn. 1994, 67, 792-799.
62. Kano, D.; Minakata, S.; Komatsu, M. J. Chem. Soc., Perkin Trans. 1 2001, 3186-3188.
63. Herse, C.; Bas, D.; Krebs, F. C.; Buergi, T.; Weber, J.; Wesolowski, T.; Laursen, B. W.; Lacour, J. Angew. Chem., Int. Ed. 2003, 42, 3162-3166.
64. Laleu, B.; Mobian, P.; Herse, C.; Laursen, B. W.; Hopfgartner, G.; Bernardinelli, G.; Lacour, J. Angew. Chem., Int. Ed. 2005, 44, 1879-1883.
65. Laleu, B.; Machado, M. S.; Lacour, J. Chem. Commun. 2006, 2786-2788.
66. Vachon, J.; Lacour, J. Chimia 2006, 60, 266-275.
67. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013-3028.
68. Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518-525.
69. O'Donnell, M. J. Acc. Chem. Res. 2004, 37, 506-517.