Direct α-iodination of aryl alkyl ketones by elemental iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Synthesis

Volumn , Issue 6, 2003, Pages 853-858

  Jereb, Marjan ^a   Stavber, Stojan ^a   Zupan, Marko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Fluorine; Iodine; Ketones; Regioselectivity

Indexed keywords

AROMATIC RINGS;

IODINE; KETONES; METHANOL; ORGANIC SOLVENTS;

SYNTHESIS (CHEMICAL);

1 CHLOROMETHYL 4 FLUORO 1,4 DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE); 2 ACETYLBENZOFURAN; 3 ACETYLINDOLE; ACETOPHENONE DERIVATIVE; ALKYL ARYL KETONE; FLUORINE DERIVATIVE; IODINE; METHANOL; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; INFRARED SPECTROSCOPY; IODINATION; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037691717     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
2. (b) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.; Liu, F. Chem Rev. 1996, 96, 365.
3. Sovak, M. Radiocontrast Agents, Handbook of Experimental Pharmacology, 73; Springer: Berlin, 1993.
4. Seevers, R. H.; Counsell, R. E. Chem Rev. 1982, 82, 575.
5. (a) Merkushev, E. B. Synthesis 1988, 923.
6. (b) Sasson, Y. Formation of Carbon-Halogen Bonds (Cl, Br, I), In The Chemistry of Functional Groups: The Chemistry of Halides, Pseudo Halides and Azides, Suppl. D2, Part 2; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1995, 535-620.
7. (c) Steel, P. G. Halobenzenes, In Rodd's Chem. Carbon Compd, 2nd ed., Vol. 3(1); Sainsburry, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
8. (d) Barluenga, J. Pure Appl. Chem. 1999, 71, 431.
9. Okamoto, T.; Kakinami, T.; Nishimura, T.; Hermawan, I.; Kajigaeshi, S. Bull. Chem. Soc. Jpn. 1992, 65, 1731.
10. Horiuchi, C. A.; Kiji, S. Bull. Chem. Soc. Jpn. 1997, 70, 421.
11. Whang, J. P.; Yang, S. G.; Kim, Y. H. Chem. Commun. 1997, 1355.
12. Barluenga, J.; Martinez-Gallo, J. M.; Najera, C.; Yus, M. Synthesis 1987, 678.
13. Bakaert, A.; Barberan, O.; Gervais, M.; Brion, J. D. Tetrahedron Lett. 2000, 41, 2903.
14. Sket, B.; Zupet, P.; Zupan, M.; Dolenc, D. Bull. Chem. Soc. Jpn. 1989, 62, 3406.
15. (a) Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron Lett. 1997, 38, 6305.
16. (b) Stavber, S.; Kralj, P.; Zupan, M. Synlett 2002, 598.
17. (c) Stavber, S.; Kralj, P.; Zupan, M. Synthesis 2002, 1513.
18. Stavber, S.; Jereb, M.; Zupan, M. Chem. Commun. 2002, 488.
19. (a) Organofluorine Compounds in Methods of Organic Chemistry (Houben-Weyl), Vol. E 10a/10b: Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Thieme: New York, 1999.
20. (b) Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431.
21. (c) Furin, G. G.; Fainzilberg, A. A. Russian Chem. Rev. 1999, 68, 653.
22. (a) Banks, R. E.; Lawrence, N. J.; Popplewell, A. L. Synlett 1994, 831.
23. (b) Stavber, S.; Kralj, P.; Zupan, M. Synlett 2001, 1152.
24. (c) Stavber, S.; Kralj, P.; Zupan, M. Acta Chim. Slov. 2002, 49, 553.
25. (d) Liu, J.; Wong, C.-H. Tetrahedron Lett. 2002, 43, 3915.
26. (e) Liu, J.; Wong, C.-H. Tetrahedron Lett. 2002, 43, 4037.
27. (a) Gilicinski, A. G.; Pez, G. P.; Syvret, R. G.; Lal, G. S. J. Fluorine Chem. 1992, 59, 157.
28. (b) Differding, E.; Bersier, P. M. Tetrahedron 1992, 48, 1595.
29. (c) Girina, G. P.; Faizil'berg, A. A.; Feoktistov, L. G. Russ. J. Electrochem. 2000, 36, 162.