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Dehydrogenative Azolation of Arenes in a Microflow Electrochemical Reactor

Laura Buglioni, Marko Beslać, Timothy Noël

2021The Journal of Organic Chemistry34 citationsDOIOpen Access PDF

Abstract

The electrochemical synthesis of aryl azoles was performed for the first time in a microflow reactor. The reaction relies on the anodic oxidation of the arene partners making these substrates susceptible for C-H functionalization with azoles, thus requiring no homogeneous transition-metal-based catalysts. The synthetic protocol benefits from the implementation of a microflow setup, leading to shorter residence times (10 min), compared to previously reported batch systems. Various azolated compounds (22 examples) are obtained in good to excellent yields.

Topics & Concepts

ElectrochemistryResidence time (fluid dynamics)Combinatorial chemistryHomogeneousCatalysisChemistrySurface modificationArylOrganic chemistryPhysical chemistryElectrodeThermodynamicsAlkylPhysicsEngineeringGeotechnical engineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Dehydrogenative Azolation of Arenes in a Microflow Electrochemical Reactor | Litcius