Expedient synthesis of gem -dialkylbenzyl heterocycles through olefinic hydroarylation

A robust approach to gem-dialkylbenzyl heterocycles has been developed through a triflic acid-catalyzed hydroarylation of olefinic heterocycles. A broad range of substrates containing pyridine, quinoline, pyrazole, triazole and imidazole moieties are shown to be highly compatible with this method. This rapid construction of gem-dialkyl groups should be useful in the synthesis of drug-like molecules containing heterocyclic diversity and in the study of the gem-dialkyl effect.