Chichibabin pyridinium synthesis <i>via</i> oxidative decarboxylation of photoexcited α-enamine acids
Zhiqiang Pan, Fengchi Hu, Di Jiang, Yuchang Liu, Chengfeng Xia
Abstract
A visible light-induced decarboxylative Chichibabin pyridinium synthesis between α-amino acids and aldehydes was developed. When the in situ generated α-enamine acids were photoexcited, they were oxidized by aerobic oxygen to give radical cation species. After decarboxylation and further oxidation, the generated iminium undergoes Chichibabin cyclization to afford pyridiniums. This photochemical protocol enables the synthesis of various tetra-substituted pyridiniums and related natural products in one-step.
Topics & Concepts
EnaminePyridiniumDecarboxylationChemistryOxidative phosphorylationOxidative decarboxylationOrganic chemistryCombinatorial chemistryCatalysisBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry