Intermolecular Hydroalkoxylation and Hydrocarboxylation of 2-Azadienes with High Efficiency
Juan M. I. Serviano, Erik J. T. Phipps, Patrick L. Holland
Abstract
Described here is a method for intermolecular hydroalkoxylation and hydrocarboxylation of 2-azadienes through cobalt-catalyzed hydrogen atom transfer and oxidation. This protocol provides a source of 2-azaallyl cation equivalents under mild conditions, is chemoselective in the presence of other C═C double bonds, and requires no excess amount of added alcohol or oxidant. Mechanistic studies suggest that the selectivity arises from lowering the transition state that leads to the highly stabilized 2-azaallyl radical.
Topics & Concepts
ChemistryIntermolecular forceSelectivityCatalysisHydrogen atomCombinatorial chemistryHydrogen bondPhotochemistryMedicinal chemistryOrganic chemistryMoleculeAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions