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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Published in | Chemical science (Cambridge) Vol. 4; no. 3; pp. 1216 - 122 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
04.02.2013
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Online Access | Get full text |
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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. |
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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 |