Mild oxidation of diarylacetylenes to 1,2-diketones using oxone in trifluoroacetic acid

Synthesis

Volumn , Issue 13, 2009, Pages 2155-2162

  Chu, Jean Ho ^a   Chen, Yen Ju ^b   Wu, Ming Jung ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

1,2 diketone; Diarylalkyne; Oxidation; Oxone

Indexed keywords

1,2-DIKETONE; DIARYLACETYLENES; DIARYLALKYNE; DIKETONES; METHANONE; MILD OXIDATION; OXONE; PHENYLETHYNYL; TRIFLUOROACETIC ACIDS;

ACIDS; BENZENE; KETONES;

OXIDATION;

1 (2 BROMOPHENYL) 2 (2 TRIFLUOROMETHYLPHENYL)ETHANE 1,2 DIONE; 1 (2 CYANOPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (2 FLUOROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (2 NITROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (2 TRIFLUOROMETHYLPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (3 NITROPHENYL) 2 4 TOLYLETHANE 1,2 DIONE; 1 (3 NITROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 ACETYLPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 BROMOPHENYL) 2 (2 TRIFLUOROMETHYLPHENYL)ETHANE 1,2 DIONE; 1 (4 BROMOPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 CHLOROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 CYANOPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 HYDROXYPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 METHOXYPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 NITROBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 1 (4 NITROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 BENZOYLBENZO[C]ISOXAZOL 3(1H) ONE; 1 PHENYL 2 4 TOLYLETHANE 1,2 DIONE; 1,2 DI 4 TOLYLETHANE 1,2 DIONE; 1,2 DIPHENYLETHANE 1,2 DIONE; 2 (2 NITROPHENYL) 1 (4 NITROPHENYL)ETHANE 1,2 DIONE; 4 (2 OXO 2 PHENYLACETYL)PHENYL ACETATE; ACETYLENE DERIVATIVE; BENZO[C]ISOXAZOL 3 YL(4 NITROPHENYL)METHANONE; KETONE DERIVATIVE; OXIDIZING AGENT; SODIUM PEROXIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; RING OPENING; ROOM TEMPERATURE; SONOGASHIRA REACTION; X RAY CRYSTALLOGRAPHY;

EID: 67651083205     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216800     Document Type: Article

References (39)

1. (a) Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1996, 61, 3888.
2. (b) Li, X.; Zhao, G.; Cao, W.-G. Chin. J. Chem. 2006, 24, 1402.
3. (a) Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. L. Org. Lett. 2004, 6, 1453.
4. (b) Deng, X.; Mani, N. Org. Lett. 2006, 8, 269.
5. (a) Bhosale, R. S.; Sarda, S. E.; Ardhapure, S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P. Tetrahedron Lett. 2005, 46, 7183.
6. (b) Hui, X.; Desrivot, J.; Bories, C.; Loiseau, P. M.; Franck, X.; Hocquemiller, R.; Figadère, B. Bioorg. Med. Chem. 2006, 16, 815.
7. Boyer, J.; Bernardes-Genisson, V.; Nepveu, F. J. Chem. Res., Synop. 2003, 507.
8. Mousset, C.; Giraud, A.; Provot, O.; Hamze, A.; Bignon, J.; Liu, J.-M.; Thoret, S.; Dubois, J.; Brion, J.-D.; Alami, M. Bioorg. Med. Chem. Lett. 2008, 18, 3266.
9. Sessler, J.; Cho, D.-G. Org. Lett. 2008, 10, 73.
10. (a) Kósa, C.; Lukáč, I.; Weiss, R. G. Macromolecules 2000, 33, 4015.
11. (b) Mosnáček, J.; Weiss, R. G.; Lukáč, I. Macromolecules 2002, 35, 3870.
12. (c) Mosnáček, J.; Lukáč, I.; Chromik, Š.; Kostič, I.; Hrdlovič, P. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 765.
13. (d) Mosnáček, J.; Weiss, R. G.; Lukáč, I. Macromolecules 2004, 37, 1304.
14. (e) Kósa, C.; Mosnáček, J.; Lukáč, I.; Hrdlovič, P.; Chmela, Š.; Habicher, W. D. J. Appl. Polym. Sci. 2006, 100, 4420.
15. (f) Husár, H.; Commereuc, S.; Lukáč, I.; Chmela, Š.; Nedelec, J. M.; Baba, M. J. Phys. Chem. B 2006, 110, 5315.
16. (g) Husár, H.; Lukáč, I. J. Photochem. Photobiol., A 2008, 195, 191.
17. (h) Corrales, T.; Catalina, F.; Peinando, C.; Allen, N. S. J. Photochem. Photobiol., A 2003, 159, 103.
18. For related papers on the synthesis of 1,2-diketones, see: (a) Yusubov, M. S.; Krasnokutskaya, E. A.; Vasilyeva, V. P.; Filimonov, V. D.; Chi, K.-W. Bull. Korean Chem. Soc. 1995, 16, 86.
19. (b) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7728.
20. (c) Che, C.-M.; Yu, W.-Y.; Chan, P.-M.; Cheng, W.-M.; Peng, S.-M.; Lau, K.-C.; Li, W.-K. J. Am. Chem. Soc. 2000, 122, 11380.
21. (d) Yusubov, M. S.; Zholobova, G. A.; Vasilevsky, S. F.; Tretyakov, E. V.; Knight, D. W. Tetrahedron 2002, 58, 1607.
22. (e) Khurana, J. M.; Kandpal, B. M. Tetrahedron Lett. 2003, 44, 4909.
23. (f) Ryu, J. Y.; Heo, S.; Park, P.; Nam, W.; Kim, J. Inorg. Chem. Commun. 2004, 7, 534.
24. (g) Antoniotti, S.; Dučach, E. Eur. J. Org. Chem. 2004, 3459.
25. (h) Chang, C.-L.; Kumar, M.-P.; Liu, R.-S. J. Org. Chem. 2004, 69, 2793.
26. (i) Mosnáček, J.; Lukáč, I. Chem. Listy 2005, 99, 421; and references cited therein.
27. (j) Katritzky, A. R.; Zhang, D.; Kirichenko, K. J. Org. Chem. 2005, 70, 3271.
28. (k) Wan, Z. W.; Jones, C. D.; Mitchell, D.; Pu, J. Y.; Zhang, T. Y. J. Org. Chem. 2006, 71, 826.
29. (l) Giraud, A.; Provot, O.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Tetrahedron 2006, 62, 7667.
30. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
31. The crystal structures of compound 2o [CCDC 716035] and compound 4 [CCDC 716034] have been deposited at the Cambridge Crystallographic Data Centre. The data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].
32. A similar 'double oxidation' mechanism of alkynes has led to 1,2-diketones, see: (a) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7728.
33. (b) Stille, J. K.; Whitehurst, D. D. J. Am. Chem. Soc. 1964, 86, 4871.
34. Wille, U.; Andropof, J. Aust. J. Chem. 2007, 60, 420.
35. Aitken, R. A.; Cadogan, J. I.; Gosney, I. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 101, 281.
36. Demir, A. S.; Reis, Tetrahedron 2004, 60, 3803.
37. Wang, X.; Zhang, Y. Tetrahedron 2003, 59, 4201.
38. Boyer, J.; Bernardes-Genisson, V.; Farines, V.; Souchard, J.-P.; Nepveu, F. Free Radical Res. 2004, 38, 459.
39. Bakke, J. M. Acta Chem. Scand., Ser. B 1975, 29, 1063.