Synthesis of 2-Fluoroalkylated Pyridines and Fluoropyridines by Thermal Denitrogenation of N -Fluoroalkyl-1,2,3-triazoles and Cyclization of Ketenimines

2026/01/22 by S. Voltrová, Blanka Klepetářová, Petr Beier · 1 voice
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Click Chemistry and Applications #Fluorine in Organic Chemistry #Synthesis and Reactivity of Heterocycles

paper · pdf · doi:10.1021/acs.joc.5c03046

openalex publication_date 2026/01/22 · openalex created_date 2026/01/24 · openalex updated_date 2026/08/01

Abstract

High Resolution Image Download MS PowerPoint Slide 2-Fluoro-6-fluoroalkylpyridines and their ring-fused analogues were synthesized from N -fluoroalkyl-4-alkenyl-1,2,3-triazoles by thermal denitrogenation, fluorine shift, cyclization, and hydrogen fluoride elimination. This reaction proceeds via ketenimine intermediates. Conversely, 2-fluoroalkylpyridines were prepared starting from N -fluoroalkyl-4-alkyl-1,2,3-triazoles and proceeded by denitrogenation, fluorine shift, hydride shift, cyclization, and hydrogen fluoride elimination. Nucleophilic aromatic substitution of 2-fluoro-6-fluoroalkylpyridines afforded highly functionalized 2-fluoroalkylpyridines.

Discussions

• #research #fluorinechem #orgchem Synthesis of 2-Fluoroalkylated Pyridines and Fluoropyridines by Thermal Denitrogenation of N-Fluoroalkyl-1,2,3-triazoles and Cyclization of Ketenimines (Voltrová, Bei [bsky, 2 points, 0 comments]

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