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 direct...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2002-03 (5), p.488-489
Main Authors: Stavber, Stojan, Jereb, Marjan, Zupan, Marko
Format: Article
Language:English
Subjects:
Diazonium Compounds
Hydrocarbons, Aromatic - chemistry
Hydrocarbons, Iodinated - chemistry
Indoles - chemistry
Iodine - chemistry
Ketones - chemistry
Solvents - chemistry
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Summary: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.
ISSN:1359-7345
DOI:10.1039/b200240j