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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| Published in | Journal of the American Chemical Society Vol. 134; no. 26; pp. 10795 - 10798 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
04.07.2012
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. The synthesis of aryl fluorides has been a topic of considerable interest 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 aryl copper(III) fluoride. 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.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. |
| Author | Hartwig, John F. Fier, Patrick S. |
| AuthorAffiliation | University of California, Berkeley |
| AuthorAffiliation_xml | – name: University of California, Berkeley |
| Author_xml | – sequence: 1 givenname: Patrick S. surname: Fier fullname: Fier, Patrick S. – sequence: 2 givenname: John F. surname: Hartwig fullname: Hartwig, John F. email: jhartwig@berkeley.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22709145$$D View this record in MEDLINE/PubMed |
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| Snippet | The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The... The synthesis of aryl fluorides has been a topic of considerable interest because of the importance of aryl fluorides in pharmaceuticals, agrochemicals and... |
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| SubjectTerms | 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 |
| Title | Copper-Mediated Fluorination of Aryl Iodides |
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