Hydrogen-bond donor and acceptor cooperative catalysis strategy for cyclic dehydration of diols to access O-heterocycles
Huan Wang, Yanfei Zhao, Fengtao Zhang, Zhengang Ke, Buxing Han, Junfeng Xiang, Zhenpeng Wang, Zhimin Liu
Abstract
, and affords a series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines, dioxanes, and thioxane in high yields. Mechanism investigation indicates that the IL cation and anion serve as hydrogen-bond donor and acceptor, respectively, to activate the C─O and O─H bonds of alcohol via hydrogen bonds, which synergistically catalyze dehydrative cyclization of diols to O-heterocycles. Notably, the products could be spontaneously separated after reaction because of their immiscibility with the IL, and the IL could be recycled. This green strategy has great potential for application in industry.
Topics & Concepts
CatalysisHydrogen bondIonic liquidAcceptorDehydrationChemistryHydrogenIonic bondingOrganic chemistryCombinatorial chemistryPolymer chemistryMoleculeIonBiochemistryCondensed matter physicsPhysicsIonic liquids properties and applicationsChemical Synthesis and ReactionsAsymmetric Hydrogenation and Catalysis