Highly efficient and clean method for direct α-iodination of aromatic ketones

Synthesis

Volumn , Issue 20, 2007, Pages 3113-3116

  Yin, Guodong ^a   Gao, Meng ^a   She, Nengfang ^a   Hu, Shengli ^a   Wu, Anxin ^a   Pan, Yuanjiang ^b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

iodo ketones; Aromatic ketones; Iodine; Multifunctional reagent; Self sorting

Indexed keywords

AROMATIC KETONES; MULTIFUNCTIONAL REAGENT;

COPPER OXIDES; FUNCTIONAL GROUPS; IODINE COMPOUNDS; REACTION KINETICS;

KETONES;

1 (2 IODO 1,1 DIMETHOXYETHYL) 4 NITROBENZENE; 1 (3 HYDROXYPHENYL) 2 IODOETHANONE; 1 (4 ETHOXYPHENYL) 2 IODOETHANONE; 1 BIPHENYL 4 YL 2 IODOETHANONE; 2 IODO 1 (6 METHOXY 2 NAPHTHYL)ETHANONE; ALPHA IODOKETONE DERIVATIVE; COPPER OXIDE; IODINE; KETONE DERIVATIVE; METAL OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; IODINATION; METHODOLOGY;

EID: 35548965056     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983880     Document Type: Article

References (35)

1. Erian, A. W.; Sherif, S. M.; Gaber, H. M. Molecules 2003, 8, 793.
2. Seevers, R. H.; Counsell, R. E. Chem. Rev. 1982, 82, 575.
3. Cardillo, G.; Shimizu, M. J. Org. Chem. 1977, 42, 4268.
4. (a) Dolenc, D. Synth. Commun. 2003, 33, 2917.
5. (b) Cort, A. D. J. Org. Chem. 1991, 56, 6708.
6. (c) Rubottom, G. M.; Mott, R. C. J. Org. Chem. 1979, 44, 1731.
7. Vankar, Y. D.; Kumaravel, G. Tetrahedron Lett. 1984, 25, 233.
8. Okamoto, T.; Kakinami, T.; Nishimura, T.; Hermawan, I.; Kajigaeshi, S. Bull. Chem. Soc. Jpn. 1992, 65, 1731.
9. Barluenga, J.; Marco-Arias, M.; González-Bobes, F.; Ballesteros, A.; González, J. M. Chem. Commun. 2004, 2616.
10. Barluenga, J.; Martinez-Gallo, J. M.; Najera, C.; Yus, M. Synthesis 1986, 678.
11. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 1 1982, 235.
12. Horiuchi, C. A.; Satoh, J. Y. Synthesis 1981, 312.
13. The method was limited to aliphatic ketones: (a) Horiuchi, C. A.; Kiji, S. Bull. Chem. Soc. Jpn. 1997, 70, 421.
14. (b) Horiuchi, C. A.; Kiji, S. Chem. Lett. 1988, 31.
15. (a) Pavlinac, J.; Stavber, S.; Zupan, M. Synthesis 2006, 2603.
16. (b) Pavlinac, J.; Stavber, S.; Zupan, M. J. Org. Chem. 2006, 71, 1027.
17. (c) Jereb, M.; Stavber, S.; Zupan, M. Synthesis 2003, 853.
18. (d) Stavber, S.; Jereb, M.; Zupan, M. Chem. Commun. 2002, 488.
19. Bekaert, A.; Barberan, O.; Gervais, M.; Brion, J. D. Tetrahedron Lett. 2000, 41, 2903.
20. Whang, J. P.; Yang, S. G.; Kim, Y. H. Chem. Commun. 1997, 1355.
21. (a) Rao, M. L. N.; Jadhav, D. N. Tetrahedron Lett. 2006, 47, 6883.
22. (b) Le Bras, G.; Provot, O.; Bekaert, A.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Synthesis 2006, 1537.
23. (c) Lee, J. C.; Park, J. Y.; Yoon, S. Y.; Bae, Y. H.; Lee, S. J. Tetrahedron Lett. 2004, 45, 191.
24. (d) Lee, J. C.; Bae, Y. H. Synlett 2003, 507.
25. (e) Lee, J. C.; Jin, Y. S. Synth. Commun. 1999, 29, 2769.
26. Kim, K. M.; Chung, K. H.; Kim, J. N.; Ryu, E. K. Synthesis 1993, 283.
27. Fukuyama, N.; Nishino, H.; Kurosawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 4363.
28. (a) Meshram, H. M.; Reddy, P. N.; Vishnu, P.; Sadashiv, K.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 991.
29. (b) Yang, D.; Yan, Y. L.; Lui, B. J. Org. Chem. 2002, 67, 7429.
30. (c) Kang, J.; Lee, J. H.; Noh, S. B.; Oh, C. S.; Kim, H. Y.; Chung, B. Y. Synlett 1990, 153.
31. (d) Curran, D. P.; Chen, M. S.; Spletzer, E.; Seong, C. M.; Chang, C. T. J. Am. Chem. Soc. 1989, 111, 8872.
32. Yin, G. D.; Zhou, B. H.; Meng, X. G.; Wu, A. X.; Pan, Y. J. Org. Lett. 2006, 8, 2245.
33. +, which was produced by treatment of iodine with methanol, could initiate the reaction; see: (a) Cruickshank, F. R.; Benson, S. W. J. Phys. Chem. 1969, 73, 733.
34. (b) Togo, H.; Iida, S. Synlett 2006, 2159.
35. Zacuto, M. J.; Cai, D. Tetrahedron Lett. 2005, 46, 447.