Abnormal and direct para-trifluoroacetylation of branched alkyl phenyl ketones by magnesium-promoted reductive aromatic substitution

Synlett

Volumn , Issue 3, 2012, Pages 401-404

  Maekawa, Hirofumi ^a   Ozaki, Taro ^a   Zulkeflee, Dayana ^a   Murakami, Taro ^a   Kihara, Shin ^a   Nishiguchi, Ikuzo ^a  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

cross coupling; electron transfer; magnesium; reduction; trifluoroacetylation

Indexed keywords

1 [4 (1 ETHOXY 2,2,2 TRIFLUORO 1 TRIMETHYLSILOXYETHYL)PHENYL] 2 METHYLPROPAN 1 ONE; 2 METHYL 1 (4 TRIFLUOROACETYLPHENYL)PROPAN 1 ONE; ACETOPHENONE; ALKYL PHENYL KETONE; BENZOPHENONE; BENZOPHENONE DERIVATIVE; CHLOROTRIMETHYLSILANE; CYCLOPROPANE; DIKETONE; ETHYL PARA TOLYL KETONE; MAGNESIUM; N METHYL 2 PYRROLDINONE; N,N DIMETHYLFORMAMIDE; TETRABUTYLAMMONIUM; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ACETYLATION; ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; CROSS COUPLING REACTION; DESILYLATION; ELECTRON TRANSPORT; ELECTROPHILICITY; GRIGNARD REACTION; HYDROLYSIS; OXIDATION; REDUCTION; SUBSTITUTION REACTION;

EID: 84856610922     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290325     Document Type: Article

References (31)

1. Moilliet J S., J. Fluorine Chem. 2001 109 13
2. Umemoto T, Fukami S, Tomizawa G, Harasawa K, Kawada K, Tomioka K, J. Am. Chem. Soc. 1990 112 8563
3. Singh R P., Shreeve J M., Synthesis 2002 2561
4. Hayashi M, Hashimoto S, Noyori R, Chem. Lett. 1984 1747
5. Yoneda N, Fukuhara T, Yamagishi K, Suzuki A, Chem. Lett. 1987 1675
6. Munyemana F, Frisque-Hesbain A.-M, Devos A, Ghosez L, Tetrahedron Lett. 1989 30 3077
7. Itoh Y, Mikami K, J. Fluorine Chem. 2006 127 539
8. Mizuta S, Shibata N, Hibino M, Nagano S, Nakamura S, Toru T, Tetrahedron 2007 63 8521
9. Kawai H, Kusuda A, Mizuta S, Nakamura S, Funahashi Y, Masuda H, Shibata N, J. Fluorine Chem. 2009 130 762
10. Keumi T, Shimada M, Takahashi M, Kitajima H, Chem. Lett. 1990 783
11. Mo J, Xu L, Xiao J, J. Am. Chem. Soc. 2005 127 751
12. Creary X, J. Org. Chem. 1987 52 5026
13. Zhu L, Miao Z, Sheng C, Yao J, Zhuang C, Zhang W, J. Fluorine Chem. 2010 131 800
14. Kiselyov A S., Harvey R G., Tetrahedron Lett. 1995 36 4005
15. Ruiz J, Astruc D, Gilbert L, Tetrahedron Lett. 1996 37 4511
16. Salazar J, López S E., Rebollo O, J. Fluorine Chem. 2003 124 111
17. López S E., Pérez Y, Restrepo J, Salazar J, Charris J, J. Fluorine Chem. 2007 128 566
18. Prashad M, Hu B, Har D, Repic O, Blacklock T J., Tetrahedron Lett. 2000 41 9957
19. Ohtaka J, Sakamoto T, Kikugawa Y, Tetrahedron Lett. 2009 50 1681
20. Gassman P G., OReilly N J., J. Org. Chem. 1987 52 2481
21. Peláez W J., BurgosPaci M A., Argüello G A., Tetrahedron Lett. 2009 50 1934
22. Kim J, Jang D O., Tetrahedron Lett. 2010 51 683
23. Ohno T, Sakai M, Ishino Y, Shibata T, Maekawa H, Nishiguchi I, Org. Lett. 2001 3 3439
24. Maekawa H, Ozaki T, Nishiguchi I, Tetrahedron Lett. 2010 51 796
25. Aprotic polar solvent is required for this coupling reaction. Use of DMF as a solvent gave better yield of coupling compounds than that of NMP.
26. Only para -substituted compounds were isolated while ortho -substituted ones can not be detected by gas chromatography. The reason is not clear, but it may be attributed to steric effects between the acyl group on the benzene ring and the acetal of trifluoroacetyl group.
27. Mandell L, Johnston J C., Day R A. Jr., J. Org. Chem. 1978 43 1616
28. Brieger G, Nestrick T J., Fu T H., J. Org. Chem. 1979 44 1876
29. Aulenta F, Hölemann A, Reißig H.-U, Eur. J. Org. Chem. 2006 1733
30. Prabhu U D. G., Eapen K C., Tamboraki C, J. Org. Chem. 1984 49 2792
31. Marsilje T H., Hedrick M P., Desharnais J, Tavassoli A, Zhang Y, Wilson I A., Benkovic S J., Boger D L., Bioorg. Med. Chem. 2003 11 4487