Selectfluor F-TEDA-BF4 mediated and solvent directed iodination of aryl alkyl ketones using elemental iodine.
Reactions of aryl alkyl ketones with methanol solution of elemental iodine and 1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4) result in the formation of corresponding alpha-iodo ketones, while switch over of the regioselectivity can be directed by using acetonitrile as the solvent and selective iodination of the aromatic site of target molecules is thus achieved.
Stavber
Stojan
S
Laboratory for Organic and Bioorganic Chemistry, Jozef Stefan Institute, Department of Chemistry, University of Ljubljana, Jamova 39, 1000 Ljubljana, Slovenia. stojan.stavber@ijs.si
Jereb
Marjan
M
Zupan
Marko
M
D003979:Diazonium Compounds; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D003979:Diazonium Compounds; D006841:Hydrocarbons, Aromatic; D006847:Hydrocarbons, Iodinated; D007211:Indoles; D007659:Ketones; D012997:Solvents; C408750:selectfluor; D007455:Iodine