Direct α-iodination of ketones using iodine/SeO2

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2903-2905

  Bekaert, Alain ^a   Barberan, Olivier ^a   Gervais, Marina ^a   Brion, Jean Daniel ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; KETONE; OXIDE; SELENIUM;

ARTICLE; IODINATION; OXIDATION; REACTION ANALYSIS;

EID: 0034655461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00310-5     Document Type: Article

References (20)

1. De Kimpe, N.; Verhe, R. In The chemistry of α-haloketones, α-haloaldehydes and α-haloimines; Patai, S.; Rappoport, Z., Eds.; John Wiley Interscience: New York, 1988; pp. 36-37.
2. Wade, L. G. Compendium of Organic Synthetic Methods, John Wiley & Sons: New York, 1984; Vol. 5, p. 508;
3. (b) Cardillo, G., Shimizu, M. J. Org. Chem. 1977, 42, 4268-4270.
4. (a) Motohashi, S.; Satomi, M.; Fujimoto, Y.; Tatsuno, T. Synthesis 1982, 1021-1023;
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7. Rubottom, G. M.; Mott, R. C. J. Org. Chem. 1979, 44, 1731-1734.
8. (a) Horiuchi, C. A.; Satoh, J. Y. Synthesis 1981, 312-314;
9. (b) Horiuchi, C. A. Kiji, S. Chem. Lett. 1988, 31-34.
10. Sket, B.; Zupan, M. Bull. Chem. Soc. Jpn. 1987, 60, 4489-4491.
11. Curran, D. P. Synthesis 1988, 417-439;
12. (b) Sha, C.-K.; Jean, T.-S.; Wang, D.-C. Tetrahedron Lett. 1990, 31, 3745-3748.
13. 2O. After drying, the solvents were removed and the residue purified by column chromatography or crystallization to yield 2 (light sensitive).
14. D'Auria, M.; D'Onofrio, F.; Piancatelli, G.; Scettri, A. Synth. Commun. 1982, 12, 1127-1138.
15. Yield is expressed in analytically pure iodoketone (after purification by chromatography or crystallization).
16. Townsend, J. M.; Spencer, T. A. Tetrahedron Lett. 1971, 137-140.
17. 1H NMR (200 MHz, δ ppm): 7.53 (d, J=2.7 Hz, 1H, H8); 7.18 (d, J=8.6 Hz, 1H, H5); 7.08 (dd, J=8.6 Hz and 2.7 Hz, 1H, H6); 4.99 (t, J=3.4 Hz, 1H, H2); 3.82 (s, 3H, OMe); 3.02 (m, 1H, H4); 2.78 (dt, J=16.5 Hz and 4.0 Hz, 1H, H4); 2.16 (m, 2H, H3).
18. 1H NMR (200 MHz, δ pp): 7.94 (dd, J=7.8 Hz and 1.6 Hz, 1H, H5); 7.54 (td, J=7.6 Hz and 1.6 Hz, 1H, H7); 7.09 (t, J=7.8 Hz, 1H, H6); 7.05 (d, J=7.6 Hz, 1H, H8); 4.90 (dd, J=4.2 Hz, and 3.0 Hz, 1H, H3); 4.50 (dd, J=12.0 Hz and 4,2 Hz, 1H, H2); 4.45 (dd, J=12.0 Hz and 3.0 Hz, 1H, H2).
19. 1H NMR (200 MHz, δ ppm): 8.40 (d, J=8.7 Hz, 1H, H8); 6.85 (dd, J=8.7 Hz and 2.5 Hz, 1H, H7); 6.71 (d, J=2,5 Hz, 1H, H5); 4.96 (t, J=3.0 Hz, 1H, H2); 3.86 (s, 3H, OMe); 3.11 (m, 1H, H4); 2.82 (dt, J=17.0 and 3.8 Hz, 1H, H4); 2.15 (m, 2H, H3).
20. Ryglowski, A.; Kafarski, P. Tetrahedron 1996, 52, 10685-10692. The ratio 2h:2h′(1:1) was measured after separation by chromatography.