Advanced Synthesis & Catalysis · 2016 · 83 citations · 48 references
Natural SciencesChemistryCatalysisOrganic ChemistryReaction EngineeringHeterocycle SynthesisOrganic SynthesisCleavageKetonesPyridine ChemistryPyridine SynthesisSubstrate Scope
Abstract An expedient cleavage of the CS bond of dimethyl sulfoxide (DMSO) has been developed for the preparation of substituted pyridines from ketones. In this transformation, the co‐product formic acid was formed from ammonium formate, which acted as an important catalyst for the reaction. Notably, this transformation exhibited a broad substrate scope towards a wide variety of different ketones to give the corresponding substituted pyridines in high yields. Mechanistic studies suggested that dimethyl sulfoxide delivered a methylene fragment, which was subsequently captured in situ to give a pyridine. magnified image
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