Electrochemical Activation of Bicyclo[1.1.0]butanes
Jeremy T. Maddigan‐Wyatt, Daniil A. Knyazev, Daniel B. Werz
Abstract
Herein, we describe a novel, light, and catalyst-free electrochemical method for the activation of bicyclo[1.1.0]butanes (BCBs) enabling cycloaddition with aldehydes and arylation with arenes. This exceptionally mild strategy for BCB functionalization leverages preliminary anodic oxidation in concert with strain release to facilitate the formation of oxabicyclohexanes (oBCHs) and bis-arylated cyclobutane products. A plausible electrolytic mechanism is proposed, alongside insights garnered from mechanistic studies.
Topics & Concepts
ChemistryElectrochemistryCycloadditionSurface modificationElectrolyteCyclobutaneCombinatorial chemistryAnodeMechanism (biology)Reaction mechanismPhotochemistryAnodic oxidationMoleculeCatalysisNanotechnologyStrain (injury)Reaction conditionsRadical Photochemical ReactionsCO2 Reduction Techniques and CatalystsOxidative Organic Chemistry Reactions