One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts
Lucien D. Caspers, Julian Spils, Mattis Damrath, Enno Lork, Boris J. Nachtsheim
Abstract
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Brønsted acids enable the effective Friedel–Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
Topics & Concepts
ChemistryDiphenylmethaneAlkylationCarbon fibersAlcoholSide chainDensity functional theoryFriedel–Crafts reactionBridge (graph theory)Organic chemistryMedicinal chemistryComputational chemistryCatalysisPolymerComposite numberInternal medicineComposite materialMaterials scienceMedicineOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology