Cooperative Friedel-Crafts catalysis in heterobimetallic regime: Alkylation of aromatics by π-activated alcohols

Journal of the American Chemical Society

Volumn 127, Issue 17, 2005, Pages 6162-6163

  Choudhury, Joyanta ^a   Podder, Susmita ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AROMATIC COMPOUND; METAL COMPLEX;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION;

EID: 18244363618     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0506004     Document Type: Article

References (38)

1. (a) Olah, G. A. Friedel-Crafts and Related Reactions; Wiley-Interscience: New York, 1964; Vol. II, Part 1.
2. (b) Olah, G. A. A Life of Magic Chemistry. Autobiographical Reflections of a Nobel Prize Winner, Wiley-Interscience: New York, 2001.
3. (c) Roberts, R. M.; Khalaf, A. A. Friedel-Crafts Alkylation Chemistry. A Century of Discovery; Marcel Dekker: New York, 1984.
4. (d) Olah, G. A. J. Org. Chem. 2001, 66, 5943.
5. (e) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.
6. (a) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Vols. 1 and 2.
7. (b) Corma, A.; García, H. Chem. Rev. 2003, 103, 4307.
8. (c) Nishibayashi, Y.; Yamanashi, M.; Takagi, Y.; Hidai, M. Chem. Commun. 1997, 859.
9. (d) Malkov, A. V.; Spoor, P.; Vinader, V.; Kočovský, P. J. Org. Chem. 1999, 64, 5308 and references therein.
10. (e) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764.
11. For FC acylation with Pt(II) complexes, see: Fürstner, A.; Voigtländer, D.; Schrader, W.; Giebel, D.; Reetz, M. T. Org. Lett. 2001, 3, 417.
12. (a) Sinha, P.; Roy, S. Organometallics 2004, 23, 67.
13. (b) Banerjee, M.; Roy, S. Org. Lett. 2004, 6, 2137.
14. (c) Banerjee, M.; Roy, S. Chem. Commun. 2003, 534.
15. (d) Sinha, P.; Roy, S. Chem. Commun. 2001, 1798.
16. (e) Kundu, A.; Roy, S. Organometallics 2000, 19, 105.
17. (f) Kundu, A.; Prabhakar, M.; Vairamani, M.; Roy, S. Organometallics 1999, 18, 2782.
18. (a) Shibasaki, M. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000; pp 105-121.
19. (b) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
20. (c) van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985.
21. (d) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178.
22. (e) Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928.
23. (a) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448.
24. 2O may be placed in moderately active group; see ref 7 and Supporting Information Table S2.
25. Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 238.
26. (a) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997.
27. (b) Yamato, T.; Hideshima, C.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1991, 56, 2089.
28. (c) Deshpande, A. B.; Bajpai, A. R.; Samant, S. D. Appl. Catal. A 2001, 209, 229.
29. (a) Klei, S. R.; Golden, J. T.; Burger, P.; Bergman, R. G. J. Mol. Catal. A 2002, 189, 79.
30. (b) Janka, M.; He, W.; Frontier, A. J.; Eisenberg, R. J. Am. Chem. Soc. 2004, 126, 6864.
31. (c) Fujita, K.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525.
32. (a) Periana, R. A.; Bhalla, G.; Tenn, W. J., III; Young, K. J. H.; Liu, X. Y.; Mironov, O.; Jones, C. J.; Ziatdinov, V. R. J. Mol. Catal. A 2004, 220, 7.
33. (b) Matsumoto, T.; Taube, D. J.; Periana, R. A.; Taube, H.; Yoshida, H. J. Am. Chem. Soc. 2000, 122, 7414.
34. 6-arene complexes of Ir(III), see: (a) Torres, F.; Sola, E.; Martín, M.; López, J. A.; Lahoz, F. J.; Oro, L. A. J. Am. Chem. Soc. 1999, 121, 10632.
35. (b) White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1977, 1654.
36. (c) Grundy, S. L.; Maitlis, P. M. J. Organomet. Chem. 1984, 272, 265.
37. Dammann, C. B.; Hughey, J. L., IV; Jicha, D. C.; Meyer, T. J.; Rakita, P. E.; Weaver, T. R. Inorg. Chem. 1973, 12, 2206.
38. See Supporting Information for preliminary results.