Litcius/Paper detail

Rhodium-Catalyzed C–H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon

Jiang Nan, Jiacheng Yin, Xue Gong, Yan Hu, Yangmin Ma

2021Organic Letters37 citationsDOI

Abstract

Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.

Topics & Concepts

SynthonAnnulationChemistryBifunctionalRhodiumCatalysisReagentCarbonateCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions