Electrochemical Benzylic C(sp<sup>3</sup>)–H Direct Amidation
Anthony Choi, Oliver H. Goodrich, Alexander Atkins, Matthew D. Edwards, David Tiemessen, Michael W. George, Alastair J. J. Lennox
Abstract
High Resolution Image Download MS PowerPoint Slide Amide bonds are ubiquitous and found in a myriad of functional molecules. Although formed in a reliable and robust fashion, alternative amide bond disconnections provide flexibility and synthetic control. Herein we describe an electrochemical method to form the non-amide C–N bond from direct benzylic C(sp 3 )–H amidation. Our approach is applied toward the synthesis of secondary amides by coupling secondary benzylic substrates with substituted primary benzamides. The reaction has been scaled up to a multigram scale in flow.
Topics & Concepts
ChemistryAmideElectrochemistryCombinatorial chemistryMoleculePeptide bondPrimary (astronomy)Organic chemistryMedicinal chemistryPhysical chemistryElectrodeEnzymeAstronomyPhysicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsChemical Synthesis and Analysis