Metal-Free Synthesis of 3‑Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study

Combined experimental and theoretical
investigations into the phenyliodine
bis­(trifluoro­acetate) (PIFA)-mediated reaction of N-arylcinnamamide to produce 3-arylquinolin-2-one derivatives
have been conducted. High regioselectivity during the aryl migration
process was observed in 3,3-disubstituted acrylamides. Density functional
theory calculation was conducted in an attempt to understand the mechanism
and the origin of the regioselectivity. On the basis of both the experimental
and the theoretical results, a mechanism involving an oxidative annulation,
followed by an aryl migration, has been proposed. The annulation is
the regioselectivity determining step.