Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides
Jay P. Barbor, Vaishnavi N. Nair, Kimberly R. Sharp, Trevor D. Lohrey, Sara E. Dibrell, Tejas K. Shah, Martin J. Walsh, Sarah E. Reisman, Brian M. Stoltz
Abstract
High Resolution Image Download MS PowerPoint Slide A nickel-catalyzed N–N cross-coupling for the synthesis of hydrazides is reported. O -Benzoylated hydroxamates were efficiently coupled with a broad range of aryl and aliphatic amines via nickel catalysis to form hydrazides in an up to 81% yield. Experimental evidence implicates the intermediacy of electrophilic Ni-stabilized acyl nitrenoids and the formation of a Ni(I) catalyst via silane-mediated reduction. This report constitutes the first example of an intermolecular N–N coupling compatible with secondary aliphatic amines.
Topics & Concepts
ChemistryNickelCatalysisYield (engineering)Intermolecular forceElectrophileArylCoupling (piping)SilaneOrganic chemistryCombinatorial chemistryPolymer chemistryMoleculeMaterials scienceAlkylEngineeringMechanical engineeringMetallurgyCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms