H-bonding organocatalysed Friedel-Crafts alkylation of aromatic and heteroaromatic systems with nitroolefins

Synlett

Volumn , Issue 13, 2004, Pages 2374-2378

  Dessole, Gabriella ^a   Herrera, Raquel P ^b   Ricci, Alfredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Friedel Crafts alkylation; Indoles; Nitroolefins; Organocatalysis

Indexed keywords

ALKENE DERIVATIVE; AROMATIC COMPOUND; INDOLE DERIVATIVE; NITROOLEFIN DERIVATIVE; SOLVENT; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; FRIEDEL CRAFTS REACTION; HYDROGEN BOND; MICROWAVE IRRADIATION; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 8644250567     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832844     Document Type: Article

References (39)

1. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3727.
2. Kim, S. P.; Leach, A. G.; Houk, K. N. J. Org. Chem. 2002, 67, 4250.
3. Blokzjil, W.; Engberts, J. B. F. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 1545.
4. Wittkopp, A.; Schreiner, P. R. Chem.-Eur. J. 2003, 9, 407.
5. (a) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
6. (b) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
7. (c) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2000, 39, 1279.
8. Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
9. (a) Maher, D. J.; Connon, S. J. Tetrahedron Lett. 2004, 45, 1301.
10. (b) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 725, 12094.
11. Mase, N.; Tanaka, F.; Barbas, C. F. III Angew. Chem. Int. Ed. 2004, 43, 2420.
12. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
13. Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559.
14. Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. III Org. Lett. 2004, 6, 2527.
15. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 725, 12672.
16. For a recent review on catalytic stereoselective Friedel-Crafts alkylation reactions, see: Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem. Int. Ed. 2004, 43, 550.
17. (a) Olah, G. A.; Krishnamurty, R.; Prakash, G. K. S. Friedel-Crafts Alkylation in Comprehensive Organic Synthesis, 1st ed, Vol III; Trost, B. M.; Flemming, I., Eds.; Pergamon Press: Oxford, 1991, Chap. 1.8, 293.
18. (b) Roberts, R. M.; Khalaf, A. A. Friedel-Crafts Alkylation Chemistry; Marcel Dekker: New York, 1984.
19. (c) Friedel-Crafts Chemistry; Olah, G. A., Ed.; Wiley: New York, 1973.
20. Harrington, P. E.; Kerr, M. A. Synlett 1996, 1047.
21. Komoto, I.; Kobayashi, S. Org. Lett. 2002, 4, 1115.
22. Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett. 2003, 44, 5115.
23. Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
24. (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
25. (b) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
26. (c) Wilcox, C. S.; Kim, E.-I.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 57, 621.
27. 2: 274.1681; found: 274.1687.
28. Bordwell, F. G.; Algrim, D. J.; Harrelson, J. A. Jr. J. Am. Chem. Soc. 1988, 110, 5903.
29. Scheerder, J.; Engbersen, J. F. J.; Casnati, A.; Ungaro, R.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6448.
30. Cave, G. W. V.; Raston, C. L.; Scott, J. L. Chem. Commun. 2001, 2159; and references therein.
31. Noland, W. E.; Lange, R. F. J. Am. Chem. Soc. 1959, 81, 1203.
32. Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 4th ed.; Thieme: New York, 2001.
33. (a) Snyder, H. R.; Katz, L. J. Am. Chem. Soc. 1947, 69, 3140.
34. (b) Noland, W. E.; Harmatman, P. J. J. Am. Chem. Soc. 1954, 76, 3227.
35. (a) Bandini, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Synthesis 2002, 1110.
36. (b) Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Selva, S.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 3700.
37. (a) Hagen, T. G.; Koehler, K. F.; Codding, P. W.; Skolnick, P.; Cook, J. M. J. Med. Chem. 1990, 33, 2343.
38. (b) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993, 46, 3325.
39. (c) Mérour, J.-Y.; Mérour, A. Synthesis 1994, 767.