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Abstract
Dehydrative cyclization of diols to O-heterocycles is attractive, but acid and/or metal-based catalysts are generally required. Here, we present a hydrogen-bond donor and acceptor cooperative catalysis strategy for the synthesis of O-heterocycles from diols in ionic liquids [ILs; e.g., 1-hydroxyethyl-3-methyl imidazolium trifluoromethanesulfonate ([HO-EtMIm][OTf])] under metal-free, acid-free, and mild conditions. [HO-EtMIm][OTf] is tolerant to a wide diol scope, shows performance even better than H
2SO
4, 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 separate ....

Bruker Neo , National Natural Science Foundation Of China , Sinopharm Chemical Reagent Co , Lanzhou Institute Of Chemical Physics , Chinese Academy Of Sciences , Shanghai Co , Centre Of Green Chemistry , National Intellectual Property Administration , Technology Co , Supplementary Materials , Green Chemistry , Lanzhou Institute , Chemical Physics , Chinese Academy , Beijing Innochem Science , Sinopharm Chemical Reagent , Bruker Avance , Bruker Vertex , Ascentis Express , Creative Commons Attribution Noncommercial , National Natural Science Foundation , தேசிய இயற்கை அறிவியல் அடித்தளம் ஆஃப் சீனா , லான்ஷோ நிறுவனம் ஆஃப் இரசாயன இயற்பியல் , சீன கலைக்கழகம் ஆஃப் அறிவியல் , ஷாங்காய் இணை , தொழில்நுட்பம் இணை ,