Silver-Catalyzed Single-Carbon Insertion of Indoles with Acetophenone <i>N</i>-Triftosylhydrazones
Linxuan Li, Hongzhu Chen, Xiaolong Zhang, Karunanidhi Murali, Qingwen Zhu, Menglin Liu, Hongru Zhang, Valentine G. Nenajdenko, Xihe Bi
Abstract
Here, we report a silver carbene-enabled single-carbon insertion reaction of indoles via a one-pot, two-step sequence to deliver a dearomative quaternary center quinoline scaffold in a modular fashion. Specifically, we used N -triftosylhydrazones as masked donor–donor carbene precursors that facilitate the insertion of carbon atoms bearing various functional groups to the library of functionalized quinoline. Experimental and DFT evidence support the transient presence of a cyclopropane species and removal of protecting groups.
Topics & Concepts
CarbeneChemistryQuinolineCyclopropaneInsertion reactionAcetophenoneCatalysisCombinatorial chemistryFunctional groupCarbon fibersMedicinal chemistryPhotochemistryStereochemistryOrganic chemistryRing (chemistry)Materials scienceComposite numberComposite materialPolymerCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions