Rapid and convenient synthesis of aryl- and heteroaryl-α-hydroxy- α-trifluoromethyl acetate via Friedel-Crafts alkylation under solvent- and catalyst-free conditions

Tetrahedron Letters

Volumn 47, Issue 15, 2006, Pages 2511-2514

  Zhao, Jun Ling ^a   Liu, Li ^a   Zhang, Hai Bo ^a   Wu, Yan Chao ^a   Wang, Dong ^a   Chen, Yong Jun ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Hydroxy trifluoromethyl carboxylate; Friedel Crafts alkylation; Solvent and catalyst free

Indexed keywords

ACETIC ACID DERIVATIVE; AROMATIC COMPOUND; ARYL ALPHA HYDROXY ALPHA TRIFLUOROMETHYL ACETATE; HETEROARYL ALPHA HYDROXY ALPHA TRIFLUOROMETHYL ACETATE; INDOLE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; SYNTHESIS; TECHNIQUE;

EID: 33644887718     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.054     Document Type: Article

References (27)

1. G.A. Olah, R. Khrisnamurti, and G.K. Surya Prakashi B.M. Trost Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 293 339
2. For review on stereoselective Friedel-Crafts alkylation reaction, see: M. Bandini, A. Melloni, and A. Umani-Rouchi Angew. Chem., Int. Ed. 43 2004 550
3. A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, and T. Fukuyama J. Am. Chem. Soc. 124 2002 6552
4. F. Lei, Y.-J. Chen, Y. Sui, L. Liu, and D. Wang Synlett 2003 1160
5. Y.J. Chen, F. Lei, L. Liu, and D. Wang Tetrahedron 59 2003 7609
6. A. Ishii, V.A. Soloshonok, and K. Mikami J. Org. Chem. 65 2000 1597
7. Y.-J. Chen, C.-S. Ge, and D. Wang Synlett 2000 1429
8. K.A. Jørgensen Synthesis 2003 1117
9. S. Shirakawa, R. Berger, and J.L. Leighton J. Am. Chem. Soc. 127 2005 2858
10. G. Dessole, R.P. Herrera, and A. Ricci Synlett 2004 2374
11. B. Török, M. Abid, G. London, J. Esquibel, M. Török, S.C. Mhadgut, P. Yan, and G.K. Surya Prakash Angew. Chem., Int. Ed. 44 2005 3086
12. For a review on recent advances in solventless organic reactions, see: G.W.V. Cave, G.L. Raston, and J.L. Scott Chem. Commun. 2001 2159
13. P.T. Anastas, and J.C. Warner Green Chemistry-Theory and Practice 1998 Oxford University Press New York
14. D.W. Nelson, J. Owens, and D. Hiraldo J. Org. Chem. 66 2001 2572
15. G.K. Surya Prakash, M. Manadal, and G.A. Olah Angew. Chem., Int. Ed. 40 2001 589
16. P. Bravo, M. Crucianelli, B. Vergani, and M. Zanda Tetrahedron Lett. 39 1998 7771
17. Y. Xu, and W.R. Dolbier Jr. Tetrahedron Lett. 39 1998 9151
18. W. Zhuang, N. Gathergood, R.G. Hazell, and K.A. Jørgensen J. Org. Chem. 66 2001 1009
19. A. Corma, H. Garcia, A. Moussaif, M.J. Sabater, R. Zniber, and A. Redouuane Chem. Commun. 2002 1058
20. G.K. Surya Prakash, P. Yan, B. Torok, and G.A. Olah Synlett 2003 527
21. R. Ding, H.B. Zhang, Y.J. Chen, L. Liu, D. Wang, and C.-J. Li Synlett 2004 555
22. 13C NMR, IR and HRMS or elemental analysis.
23. K. Kato, S. Fujii, Y.-F. Gong, S. Tanaka, M. Katayama, and H. Kimoto J. Fluorine Chem. 99 1999 5
24. J.S. Yadav, B.V. Subba Reddy, Ch.V.S.R. Murthy, G. Mahesh Kumar, and Ch. Madan Synthesis 2001 783
25. J. Hao, S. Taktak, K. Aikawa, Y. Yusa, M. Hatano, and K. Mikami Synlett 2001 1443
26. C. Ramesh, J. Banerjee, R. Pal, and B. Das Adv. Synth. Catal. 345 2003 557
27. G. Bartoli, M. Bosco, G. Foglia, A. Giulani, E. Marcantoni, and L. Sambri Synthesis 2004 895