Synthesis of β-Methylsulfonylated N-Heterocycles from Saturated Cyclic Amines with the Insertion of Sulfur Dioxide
Yan He, Jintao Yang, Qimeng Liu, Xinying Zhang, Xuesen Fan
Abstract
)-H methylsulfonylation of inactivated cyclic amines with the promotion and participation of inorganic sodium metabisulfite and dicumyl peroxide (DCP) has been developed. Notably, bifunctional DCP acted not only as an oxidant to promote the dehydrogenation but also as a methyl radical to participate in the sulfone formation. With this protocol, a number of β-methylsulfonylated tetrahydropyridines, tetrahydroazepines, and pyrroles were obtained in a facile one-pot manner.
Topics & Concepts
ChemistryDehydrogenationBifunctionalSulfur dioxideSodium metabisulfiteCyclohexanoneSulfoneOrganic chemistrySulfurPeroxideHydrogen peroxideCatalysisMedicinal chemistryCombinatorial chemistrySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods