Substrate-controlled product divergence in the reaction of α-fluoro-β-ketoamides with arynes

Abstract

An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes. The reaction of secondary α-fluoro-β-ketoamides with arynes provided access to α-aryl-α-fluoroacetamides through an arylation/deacylation sequence. Interestingly, the reaction of tertiary α-fluoro-β-ketoamides resulted in the C–C σ-bond insertion reaction to afford 1,2-disubstituted arenes.