DMSO/<i>t</i>-BuONa/O<sub>2</sub>-Mediated Aerobic Dehydrogenation of Saturated <i>N</i>-Heterocycles
Ruchun Yang, Shusheng Yue, Wei Tan, Yongfa Xie, Hu Cai
Abstract
Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N–H bond or α-C–H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.
Topics & Concepts
ChemistryDehydrogenationRadicalHydrogen atom abstractionMedicinal chemistryOrganic chemistryFree-radical reactionFunctional groupNitrogenCatalysisPolymerAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions