The vinylogous Catellani reaction: a combined computational and experimental study

Abstract

In the presence of 5 mol% Pd(OAc)₂, 1 equiv. of norbornene, and K₂CO₃, the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations.