Transition-Metal-Free and Base-Promoted Carbon–Heteroatom Bond Formation via C–N Cleavage of Benzyl Ammonium Salts
Long Liu, Yuanyuan Tang, Kunyu Wang, Tianzeng Huang, Tieqiao Chen
Abstract
A facile and general method for constructing carbon–heteroatom (C–P, C–O, C–S, and C–N) bonds via C–N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
Topics & Concepts
ChemistryHeteroatomTransition metalNucleophileBond cleavageAmmoniumCarbon fibersHydrogen bondMedicinal chemistryOrganic chemistryCatalysisMoleculeRing (chemistry)Materials scienceComposite materialComposite numberCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling Reactions