Proton-catalyzed, silane-fueled Friedel-Crafts coupling of fluoroarenes

O Allemann, S Duttwyler, P Romanato…

Index: Allemann, Oliver; Duttwyler, Simon; Romanato, Paola; Baldridge, Kim K.; Siegel, Jay S. Science, 2011 , vol. 332, # 6029 p. 574 - 577

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Citation Number: 89

Abstract

Abstract The venerable Friedel-Crafts reaction appends alkyl or acyl groups to aromatic rings through alkyl or acyl cation equivalents typically generated by Lewis acids. We show that phenyl cation equivalents, generated from otherwise unreactive aryl fluorides, allow extension of the Friedel-Crafts reaction to intramolecular aryl couplings. The enabling feature of this reaction is the exchange of carbon-fluorine for silicon-fluorine bond ...