A Catalyst/Oxidant/Base Free Benzylic Csp<sup>3</sup>−H Alkoxylation of toluidines via Electro‐oxidative Csp<sup>3</sup>−O‐Coupling with Alcohols
Sushobhan Chowdhury, Shubham Pandey
Abstract
Abstract Functionalization of Csp 3 −H bond meets various challenges owing to their well‐known inertness. The task becomes even more challenging for carbon‐heteroatom coupling e. g., Csp 3 −O coupling. Herein we report an electrochemical approach for the direct regioselctive cross‐dehydrogenative hetero‐coupling of benzylic Csp 3 −H bonds of toluidines with alcohols at room temperature under external catalyst, oxidant and base‐free condition. The developed protocol utilizes benzylic substrates as the limiting reagent for the site‐selective coupling and demonstrates wide substrate scope with respect to both the coupling partners synthesizing corresponding benzylic ethers in moderate to excellent yields.
Topics & Concepts
ChemistryCatalysisReagentSubstrate (aquarium)Coupling (piping)HeteroatomElectrochemistryCombinatorial chemistryOxidative coupling of methaneBase (topology)Organic chemistryRing (chemistry)Physical chemistryElectrodeOceanographyMathematicsMathematical analysisMechanical engineeringEngineeringGeologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques