The Friedel–Crafts reaction is one of the most beloved and well used in the organic chemist's recipe book, allowing the attachment of chemical groups to aromatic rings through a carbon–carbon bond. Jay Siegel and his colleagues at the University of Zurich in Switzerland have now devised a way to attach one aromatic ring to another, which they say will allow the synthesis of more complex compounds.
Using a silicon-based reagent and an acid catalyst, the authors activated the normally stable bond between a fluorine atom and one of the carbon atoms of an aromatic ring. This led, in turn, to the formation of a new bond between the carbon and another carbon atom on a different aromatic ring. Meanwhile, the acid catalyst is regenerated to drive another cycle of the reaction.
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Fusing rings with fluorine. Nature 473, 9 (2011). https://doi.org/10.1038/473009a
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DOI: https://doi.org/10.1038/473009a