Litcius/Paper detail

A Palladium-Catalyzed Cascade C–C Activation of Cyclopropenone and Carbonylative Amination: Easy Access to Highly Functionalized Maleimide Derivatives

Tanmayee Nanda, Ponneri C. Ravikumar

2020Organic Letters41 citationsDOI

Abstract

We describe herein the first report on palladium-catalyzed C–C bond activation of cyclopropenone and concomitant carbonylative amination to produce maleimides. The interesting aspect of this reaction is that the sacrificial elimination of carbon monoxide from the substrate is efficiently recaptured by one of the intermediates in the catalytic cycle for the formation of maleimides. 18O isotopic studies confirmed that the source of carbon monoxide is from cyclopropenone.

Topics & Concepts

ChemistryMaleimidePalladiumCarbon monoxideCatalysisAminationCarbonylationSubstrate (aquarium)MonoxideCombinatorial chemistryCascade reactionCatalytic cycleIsotopic labelingOrganic chemistryOceanographyGeologyCatalytic C–H Functionalization MethodsSynthesis and Reactivity of HeterocyclesCyclopropane Reaction Mechanisms