Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline <i>N</i> ‐Oxides by Electrochemical Reductive Cyclization
Haoran Zhu, Jair N. Powell, Victoria A. Geldchen, Adam S. Drumheller, Tom G. Driver
Abstract
Electrochemical reduction of 2-allyl-substituted nitroarenes using a simple, undivided electrochemical cell with non-precious electrodes to generate nitroarene radical anions was developed. The nitroarene radical anion intermediates participate in 1,5-hydrogen atom transfer reactions to construct quinoline N-oxides bearing aryl-, heteroaryl-, alkenyl-, benzyl-, sulfonyl-, or carboxyl groups.
Topics & Concepts
QuinolineChemistryElectrochemistryAryl radicalReactivity (psychology)SulfonylArylPhotochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryElectrodeAlkylPhysical chemistryPathologyMedicineAlternative medicineRadical Photochemical ReactionsAmmonia Synthesis and Nitrogen ReductionSulfur-Based Synthesis Techniques