Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
James Harnedy, Hussain A. Maashi, Albara A. M. A. El Gehani, Matthew Burns, Louis C. Morrill
Abstract
High Resolution Image Download MS PowerPoint Slide Herein we report an electrochemical approach for the deconstructive functionalization of cycloalkanols, where various alcohols, carboxylic acids, and N -heterocycles are employed as nucleophiles. The method has been demonstrated across a broad range of cycloalkanol substrates, including various ring sizes and substituents, to access useful remotely functionalized ketone products (36 examples). The method was demonstrated on a gram scale via single-pass continuous flow, which exhibited increased productivity in relation to the batch process.
Topics & Concepts
ChemistrySurface modificationKetoneNucleophileElectrochemistryCombinatorial chemistryOrganic chemistryElectrodeCatalysisPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques