Cobalt(III)-Catalyzed Chemo- and Regioselective [4 + 2]-Annulation of Aromatic Sulfoxonium Ylides with 1,3-Diynes
Suresh Kumar Yadav, Balu Ramesh, Masilamani Jeganmohan
Abstract
Air-stable, highly abundant, and cost-effective Co(III)-catalyzed redox-neutral [4 + 2]-annulation of aromatic sulfoxonium ylides with 1,3-diynes providing useful substituted 1-naphthol derivatives in a regioselective manner is described. Further, the prepared 1-naphthols having internal alkyne were converted into useful polycarbocyclic molecules and spiro-dienone derivatives in good-to-excellent yields. A possible reaction mechanism involving ortho C–H activation as a key step was proposed and supported by deuterium labeling and kinetic isotope labeling studies.
Topics & Concepts
AnnulationChemistryRegioselectivityCatalysisAlkyneKinetic isotope effectDeuteriumCombinatorial chemistryCobaltMoleculeMedicinal chemistryPhotochemistryOrganic chemistryPhysicsQuantum mechanicsCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSulfur-Based Synthesis Techniques