Fluorination of α-Imino Gold Carbenes to Access C<sub>3</sub>-Fluorinated Aza-Heterocycles
Shashank P. Sancheti, Dibya Jyoti Mondal, Nitin T. Patil
Abstract
Reported herein is the fluorination of α-imino gold carbenes, generated in situ from azidoalkynes, to access substituted C 3 -fluorinated quinolones and indoles. The methodology has been applied for synthesizing C 3 -fluorinated quinolone- and quinoline-based natural products, including pseudanes (4 representative examples), chimanine A, and graveolinine. Mechanistic investigations, including NMR and SC-XRD analysis, reveal that NEt 3 ·3HF reacts with the gold catalyst to generate a phosphine-ligated fluoride-bridged binuclear gold complex which then generates the active catalyst for this reaction.
Topics & Concepts
QuinolineCatalysisPhosphineChemistryCombinatorial chemistryFluorideCarbeneOrganic chemistryInorganic chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms