Carbofluorination a palladium-catalyzed cascade reaction

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...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 4; no. 3; pp. 1216 - 122
Main Authors Braun, Marie-Gabrielle, Katcher, Matthew H, Doyle, Abigail G
Format Journal Article
LanguageEnglish
Published 04.02.2013
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Summary: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. This article demonstrates tandem C-C and C-F bond formation for the palladium-catalyzed carbofluorination of allenes.
Bibliography:Electronic supplementary information (ESI) available: Experimental procedures, additional reaction optimization, details for stoichiometric reactions, and spectroscopic data for all new compounds. See DOI
10.1039/c2sc22198e
ISSN:2041-6520
2041-6539
DOI:10.1039/c2sc22198e