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Synthesis of Polyfluorobiaryls via Copper-Catalyzed Decarboxylative Couplings of Potassium Polyfluorobenzoates with Aryl Bromides and Iodides

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New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation

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Abstract

In this chapter, we report a copper-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with aryl iodides and bromides. This reaction can be used for the preparation of polyfluoroaromatic compounds and polyfluorostilbene. The reactants used in the reaction are easily accessible nonvolatile polyfluorobenzoate salts. Mechanistic studies suggest that decarboxylation occurs at first on copper(I) to generate a polyfluorophenylcopper(I) intermediate, which then undergoes oxidative addition with aryl halides and reductive elimination to produce the coupling products.

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  1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, China

    Rui Shang

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Shang, R. (2017). Synthesis of Polyfluorobiaryls via Copper-Catalyzed Decarboxylative Couplings of Potassium Polyfluorobenzoates with Aryl Bromides and Iodides. In: New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-10-3193-9_3

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