Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4<i>H</i>-cinnolin-2-ium-1-ide
Xiaolan Fang, Ji Cao, Weijie Ding, Huile Jin, Xiaochun Yu, Shun Wang
Abstract
An efficient Cu(I)/DMAP/air system for the one-pot synthesis of 4-oxo-4H-cinnolin-2-ium-1-ides, which are often difficult to prepare by traditional routes from substituted 2-alkynylanilines and nitrosoarenes, was developed. These 4-oxo-4H-cinnolin-2-ium-1-ides have practical applications as mechanoluminescent materials. Preliminary mechanistic experiments were performed, and a plausible mechanism for this tandem process is proposed. The use of an inexpensive copper catalyst and molecular oxygen as the oxygen source and the oxidant make this an attractive green protocol with potential synthetic applications.
Topics & Concepts
CatalysisChemistryMechanoluminescenceTandemCombinatorial chemistryMolecular oxygenOrganic synthesisOxygenOrganic chemistryMaterials sciencePhosphorComposite materialOptoelectronicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsLuminescence and Fluorescent Materials