Current-Controlled Electrochemical Approach Toward Mono- and Trifluorinated Isoindolin-1-one Derivatives
Chenglin Ding, Qiaohong Xu, Shuai Wu, Yi Zhong, Xinglei He, Yuqi Lin, Yuanming Li, Ke‐Yin Ye
Abstract
An electrochemical intramolecular 5- exo-dig aza-cyclization of 2-alkynylbenzamides and subsequent nucleophilic fluorination have been developed to afford the highly selective synthesis of mono- and trifluorinated isoindolin-1-one derivatives. This work demonstrates the unique capability of synthetic electrochemistry in controlling reaction selectivity through the applied electrolytic parameters. In addition, the obtained monofluorinated 3-methyleneisoindolin-1-one ( 19 ) displays interesting photophysical properties that are not observed in its nonfluorinated analog.
Topics & Concepts
ChemistryElectrochemistryCurrent (fluid)Combinatorial chemistryNanotechnologyElectrodePhysical chemistryMaterials scienceElectrical engineeringEngineeringFluorine in Organic ChemistrySynthesis and Biological EvaluationOxidative Organic Chemistry Reactions