Synthetic Electrochemistry Enabled Esterification via Oxidative Mesolytic Cleavage of Alkoxyamines
Kevin Lee, Dante Gilberti, Clairissa Yom, Jacob Meza, Jamere Stewart, Michael Lee, Justin Alvarez, Abigail K. Hart, Justin Zheng, Yalan Xing
Abstract
Stable benzylic carbocations were generated via mesolytic cleavage of TEMPO-derived alkoxyamines, which was realized by electrochemical oxidation. This strategy provided an efficient and unique approach to access stabilized carbocations under mild conditions. Esterification of benzylic carbocations using carboxylic acid produced a variety of benzylic esters with a broad substrate scope and excellent functional group compatibility.
Topics & Concepts
CarbocationChemistryOxidative cleavageCleavage (geology)ElectrochemistryCombinatorial chemistryOxidative phosphorylationCarboxylic acidOrganic chemistryMaterials scienceCatalysisElectrodeBiochemistryComposite materialFracture (geology)Physical chemistryOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods