Experimental and computational studies of the mechanism of iron-catalysed C–H activation/functionalisation with allyl electrophiles
Joshua C. DeMuth, Zhihui Song, Stephanie H. Carpenter, Theresa E. Boddie, Aleksa Radović, Tessa M. Baker, Osvaldo Gutiérrez, Michael L. Neidig
Abstract
-chloromorpholine as the C-N bond-forming electrophile, reveals a rapid reaction of electrophile with an analogous C-H activated iron intermediate consistent with the inner-sphere radical process defined for the C-H allylation system, demonstrating the prevalence of this novel reaction coordinate in this sub-class of iron-catalysed C-H functionalisation systems. Overall, these results provide a critical mechanistic foundation for the rational design and development of improved systems that are efficient, selective, and useful across a broad range of C-H functionalisations.
Topics & Concepts
ElectrophileMechanism (biology)ChemistryReaction mechanismCatalysisStereochemistryOrganic chemistryPhysicsQuantum mechanicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions