Dramatic enhancement of catalytic activity in an ionic liquid: Highly practical Friedel-Crafts alkenylation of arenes with alkynes catalyzed by metal triflates

Angewandte Chemie - International Edition

Volumn 43, Issue 45, 2004, Pages 6183-6185

  Song, Choong Eui ^a   Jung, Da Un ^b   Choung, Su Yhen ^a   Roh, Eun Joo ^b   Lee, Sang Gi ^b  

^a Sungkyunkwan University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

Alkenylation; C C bond formation; Homogeneous catalysis; Ionic liquids; Lewis acids

Indexed keywords

CATALYSIS; FRIEDEL-CRAFTS REACTION; REACTION KINETICS;

ALKENYLATION; IONIC LIQUIDS; METAL TRIFLATE;

AROMATIC COMPOUNDS;

2(1H) QUINOLINONE DERIVATIVE; 4 PHENYLCOUMARIN; ALKENE; ALKYNE; AROMATIC COMPOUND; BENZENE; COUMARIN DERIVATIVE; LEWIS ACID; POLYCYCLIC AROMATIC HYDROCARBON; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; SYNTHESIS;

ALKYNES; BENZENE DERIVATIVES; CATALYSIS; IONS; LANTHANOID SERIES ELEMENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SOLVENTS;

EID: 10044248730     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460292     Document Type: Article

References (32)

1. For reviews of Friedel-Crafts alkylation reactions, see: a) Friedel-Crafts and Related Reactions, Vol. II, part 1 (Ed.: G. A. Olah), Wiley-Interscience, New York, 1964;
2. b) Friedel-Crafts Alkylation Chemistry. A Gentry of Discovery (Eds.: R. M Roberts, A. A. Khalaf), Marcel Dekker, New York, 1984;
3. c) G. A. Olah, R. Krishnamurit, G. K. S. Prakash, in Friedel-Crafts Alkylations in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991.
4. O. W. Cook, V. J. Chaber, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, J. Am. Chem. Soc. 1928, 50, 2564.
5. O. W. Cook, V. J. Chaber, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, J. Am. Chem. Soc. 1928, 50, 2564.
6. O. W. Cook, V. J. Chaber, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, J. Am. Chem. Soc. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, J. Am. Chem. Soc. 1928, 50, 2564.
7. T. Tsuchimoto, T. Maeda, E. Shirakawa, Y. Kawakami, Chem. Commun. 2000, 1573.
8. G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, G. Gnappi, Tetrahedron Lett. 1995, 36, 9177.
9. G. Casiraghi, G. Casnati, G. Puglia, G Sartori, G. Terenghi, Synthesis 1977, 122.
10. M. Yamaguchi, Y. Kido, A. Hayashi, M. Hirama, Angew. Chem. 1997, 109, 1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1313; Y. Kido, S. Yoshimura, M. Yamaguchi, T. Uchimaru, Bull. Chem. Soc. Jpn. 1999, 72, 1445.
11. M. Yamaguchi, Y. Kido, A. Hayashi, M. Hirama, Angew. Chem. 1997, 109, 1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1313; Y. Kido, S. Yoshimura, M. Yamaguchi, T. Uchimaru, Bull. Chem. Soc. Jpn. 1999, 72, 1445.
12. M. Yamaguchi, Y. Kido, A. Hayashi, M. Hirama, Angew. Chem. 1997, 109, 1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1313; Y. Kido, S. Yoshimura, M. Yamaguchi, T. Uchimaru, Bull. Chem. Soc. Jpn. 1999, 72, 1445.
13. M. Yamaguch, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 1995, 777, 1151.
14. For recent reviews on ionic liquids, see: a) C. E. Song, Chem. Commun. 2004, 1033;
15. b) R. Sheldon, Chem. Commun. 2001, 2399;
16. c) P. Wasserscheid, W. Kein, Angew. Chem. 2000, 112, 3926; Angew. Chem. Int. Ed. 2000, 39, 3772;
17. c) P. Wasserscheid, W. Kein, Angew. Chem. 2000, 112, 3926; Angew. Chem. Int. Ed. 2000, 39, 3772;
18. d) T. Welton, Chem. Rev. 1999, 99, 2071.
19. Our recent examples: a) C. E. Song, W. H. Shim, E. J. Roh, J. H. Choi, Chem. Commun. 2000, 1695;
20. b) C. E. Song, E. J. Roh, Chem. Commun. 2000, 837;
21. c) C. E. Song, W. H. Shim, E. J. Roh, S.-g. Lee, J. H. Choi, Chem. Commun. 2001, 1122;
22. d) S.-g. Lee, J. W. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698;
23. e) D. W. Kim, C. E. Song, D. Y. Chi, J. Am. Chem. Soc. 2002, 124, 10278;
24. f) S.-g. Lee, J. W. Park, Bull. Korean Chem. Soc. 2002, 23, 1367;
25. g) D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem. 2003, 68, 4281;
26. h) E. J. Kim, S. Y. Ko, C. E. Song, Helv. Chim. Acta 2003, 86, 894;
27. i) S.-g. Lee, Y. J. Zhang, P. Z. Yu, H. Yoon, C. E. Song, J. H. Choi, J. Hong, Chem. Commun. 2003, 2624;
28. j) S.-g. Lee, J. W. Park, J. Mol. Catal. A 2003, 194, 49.
29. 4] or [bmim][OTf].
30. 6] and water (1:1, v/v) without any metal triflate catalyst. However, the reaction did not occur at all.
31. A new synthetic route to alkenylated arenes involving Pd- and Pt-catalyzed addition of arenes to alkynes in the presence of trifluoroacetic acid was recently reported: a) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992;
32. b) C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc. 2000, 122, 7252.