Abstract
Lewis acid catalyzed benzylic C–H bond functionalization of alkyl-substituted azaarenes is described. The addition to <i>N</i>-tosyl imines proceeded under solvent-free conditions using various Lewis acids. Cu(OTf)<sub>2</sub> was the best Lewis acid, and 1,2-addition proceeded at 60–120 °C, giving products in 23–92% yield. On the other hand, strongly Lewis acidic rare-earth metal triflates, Sc(OTf)<sub>3</sub> and Y(OTf)<sub>3</sub>, were essential to promote the 1,4-addition of alkyl-substituted azaarenes to enones, and products were obtained in 60–96% yield.
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