Fluorination of α‑Imino Gold Carbenes to Access C3‑Fluorinated Aza-Heterocycles

Reported herein is the fluorination of α-imino gold carbenes, generated in situ from azidoalkynes, to access substituted C3-fluorinated quinolones and indoles. The methodology has been applied for synthesizing C3-fluorinated quinolone- and quinoline-based natural products, including pseudanes (4 rep...

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Bibliographic Details
Published in:ACS catalysis 2023-04, Vol.13 (7), p.4391-4397
Main Authors: Sancheti, Shashank P., Mondal, Dibya Jyoti, Patil, Nitin T.
Format: Article
Language:English
Online Access:Get full text
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Summary:Reported herein is the fluorination of α-imino gold carbenes, generated in situ from azidoalkynes, to access substituted C3-fluorinated quinolones and indoles. The methodology has been applied for synthesizing C3-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 NEt3·3HF reacts with the gold catalyst to generate a phosphine-ligated fluoride-bridged binuclear gold complex which then generates the active catalyst for this reaction.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.3c00088