Carbofluorination via a palladium-catalyzed cascade reaction
Author(s): Braun, Marie-Gabrielle; Katcher, Matthew H.; Doyle, Abigail G.
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Abstract: | This article demonstrates the first examples of tandem C–C and C–F bond formation for the palladium-catalyzed carbofluorination of allenes. The intramolecular Heck-fluorination cascade provides monofluoromethylated heteroarenes, an important class of products in medicinal chemistry. We also describe an intermolecular variant for the three-component coupling of allenes, aryl iodides, and AgF. Mechanistic studies indicate that C–F bond formation occurs by outer sphere attack of fluoride on an allylpalladium fluoride intermediate. |
Publication Date: | 4-Jan-2013 |
Citation: | Braun, Marie-Gabrielle, Katcher, Matthew H., Doyle, Abigail G. (2013). Carbofluorination via a palladium-catalyzed cascade reaction. Chemical Science, 4 (3), 1216 - 1216. doi:10.1039/c2sc22198e |
DOI: | doi:10.1039/c2sc22198e |
ISSN: | 2041-6520 |
EISSN: | 2041-6539 |
Pages: | 4, 1216 - 1216 |
Type of Material: | Journal Article |
Journal/Proceeding Title: | Chemical Science |
Version: | Final published version. Article is made available in OAR by the publisher's permission or policy. |
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