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Synthesis 2006(9): 1537-1541
DOI: 10.1055/s-2006-926435
DOI: 10.1055/s-2006-926435
PAPER
© Georg Thieme Verlag Stuttgart · New York
α-Iodination of Ketones with MnO2/I2 Reagent Combination: A New Environmentally Friendly Procedure
Further Information
Received
9 November 2005
Publication Date:
11 April 2006 (online)
Publication History
Publication Date:
11 April 2006 (online)

Abstract
In alcoholic media, α-iodination of ketones was accomplished using MnO2/I2 reagent combination in a new, environmentally friendly procedure. The reactions carried out under thermal conditions or microwave irradiation afforded α-iodo ketones in reasonable to good yields.
Key words
iodine - manganese oxide - halogenation - ketones
- 1 For a recent review, see:
Takami K.Usugi SI.Yorimitsu H.Oshima K. Synthesis 2005, 824 - 2
Ringold HJ.Stork G. J. Am. Chem. Soc. 1958, 80: 250 - 3
Takeda A.Tsuboi S.Sakai T. J. Org. Chem. 1974, 39: 2601 - 4
Motohashi S.Satomi M. Synthesis 1982, 1021 - 5
Jullian PL.Karpel WJ. J. Am. Chem. Soc. 1950, 72: 362 ; and references cited therein - 6
Bergman J.Bäckvall JE. Tetrahedron 1975, 31: 2063 -
7a
Wolff L.Greulich R. Justus Liebigs Ann. Chem. 1912, 394: 36 -
7b
McKillop A.Fowler JS.Zelesko MJ.Hunt JD.Taylor EC.McGillivray G. Tetrahedron Lett. 1969, 2427 - 8
Cambie RC.Hayward RC.Jurlina JL.Ruthledge PS.Woodgate PD. J. Chem. Soc., Perkin Trans. 1 1978, 126 -
9a
Rubottom GM.Mott RC.Juve HD. J. Org. Chem. 1981, 46: 2717 -
9b
Rubottom GM.Mott RC. J. Org. Chem. 1979, 44: 1731 - 10
D’Auria M.D’Onofrio F.Piancatelli G.Scettri A. Synth. Commun. 1982, 12: 1127 - 11
Horiuchi CA.Kiji S. Bull. Chem. Soc. Jpn. 1997, 70: 421 -
12a
Bekaert A.Barberan O.Gervais M.Brion J.-D. Tetrahedron Lett. 2000, 41: 2903 -
12b
Bekaert A.Provot O.Rasolojaona O.Alami M.Brion J.-D. Tetrahedron Lett. 2005, 46: 4187 - 13 For a recent review on Selenium chemistry, see:
Nogueira CW.Zeni G.Rocha JBT. Chem. Rev. 2004, 104: 6255 - 14
Cahiez G.Alami M. Manganese Dioxide, In Encyclopedia of Reagents for Organic Synthesis Vol. 5:Paquette L. Wiley; Chichester: 1995. p.3229 - 17
Lee JC.Bae YH. Synlett 2003, 507 - 18
Olivi N.Thomas E.Peyrat JF.Alami M.Brion JD. Synlett 2004, 2175 - 19
Moradi WA.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7996
References
We have observed that shorter reaction times (e.g., 1 h 30, 3 h 30 and 12 h) led to partial α-iodination of tetralones and after optimization, refluxing for 18 h led to better yields of iodo compounds.
16Starting materials (ketones) and α-iodo ketones were easily separated by chromatography on silica gel.