Copper-Mediated Fluorination of Aryl Iodides

The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the sy...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 26; pp. 10795 - 10798
Main Authors Fier, Patrick S., Hartwig, John F.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.07.2012
Amer Chemical Soc
Subjects
agrochemicals
aromatic hydrocarbons
Benzene Derivatives - chemistry
Chemistry
Chemistry, Multidisciplinary
Copper
drugs
fluorides
Fluorides - chemistry
Halogenation
Hydrocarbons, Fluorinated - chemical synthesis
Iodides
Physical Sciences
Science & Technology
Silver Compounds
ULLMANN CONDENSATION
HALIDES
REAGENT
PALLADIUM
MODELS
MECHANISMS
DERIVATIVES
BROMIDES
SALTS
FLUORIDE
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Summary:The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride.
Bibliography:NIH RePORTER
ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja304410x