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Catalysis for fluorination and trifluoromethylation

Abstract

Recent advances in catalysis have made the incorporation of fluorine into complex organic molecules easier than ever before, but selective, general and practical fluorination reactions remain sought after. Fluorination of molecules often imparts desirable properties, such as metabolic and thermal stability, and fluorinated molecules are therefore frequently used as pharmaceuticals or materials. But the formation of carbon−fluorine bonds in complex molecules is a significant challenge. Here we discuss reactions to make organofluorides that have emerged within the past few years and which exemplify how to overcome some of the intricate challenges associated with fluorination.

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Figure 1: Directed electrophilic palladium-catalysed Ar−F bond-forming reactions.
Figure 2: Nucleophilic palladium-catalysed Ar−F bond-forming reaction.
Figure 3: Electrophilic silver-catalysed Ar−F bond-forming reaction.
Figure 4: Transition-metal-catalysed Ar−CF 3 bond-forming reactions.
Figure 5: Catalytic enantioselective C sp 3 −F and C sp 3 −CF 3 bond-forming reactions.

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Acknowledgements

We thank the NSF (CHE-0952753) and the NIH-NIGMS (GM088237) for financial support.

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Furuya, T., Kamlet, A. & Ritter, T. Catalysis for fluorination and trifluoromethylation. Nature 473, 470–477 (2011). https://doi.org/10.1038/nature10108

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