Electro-oxidative Synthesis of Unsymmetrical Alkyne-1,4-diones via Sequential Ring Formation and Cleavage
Atreyee Halder, Debabrata Maiti, Jhilik Dutta, Suman De Sarkar
Abstract
Synthesis of unsymmetrical but-2-yne-1,4-diones is reported through oxidative alkyne translocation of readily accessible homopropargylic alcohols. The developed method consists of an unprecedented one-pot sequential electro-oxidative annulation-fragmentation-chemical selenoxide elimination process. Excellent functional group compatibility was observed, and an array of yne-1,4-diones were synthesized. Derivatization of the alkyne gave access to other valuable scaffolds. Detailed mechanistic studies through the isolation of key intermediates clarified the cascade transformation.
Topics & Concepts
ChemistryAlkyneAnnulationDerivatizationCombinatorial chemistryOxidative phosphorylationOxidative cleavageFragmentation (computing)Organic chemistryCatalysisOperating systemBiochemistryHigh-performance liquid chromatographyComputer scienceRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions