Related Experiment Video
Updated: Feb 8, 2026

Integration of 5G Experimentation Infrastructures into a Multi-Site NFV Ecosystem
Published on: February 3, 2021
Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines
Felix Scheidt1, Christian Thiehoff1, Gülay Yilmaz1
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
Abstract:
Herein, we describe a catalytic fluorooxygenation of readily accessible N-allylcarboxamides via an I(I)/I(III) manifold to generate 2-oxazolines containing a fluoromethyl group. Catalysis is conditional on the oxidation competence of Selectfluor®, whilst HF serves as both a fluoride source and Brønsted acid activator. The C(sp3)-F bond of the mono-fluoromethyl unit and the C(sp3)-O bond of the ring are aligned in a synclinal relationship thereby engaging in stabilising hyperconjugative interactions with vicinal, electron-rich σ-bonds (σC-C→σ*C-F and σC-H→σ*C-O). This manifestation of the stereoelectronic gauche effect was established by X-ray crystallographic analysis of a representative example. Given the importance of fluorine in drug discovery, its ability to modulate conformation, and the prevalence of the 2-oxazoline scaffold in Nature, this strategy provides a rapid entry into an important bioisostere class.
Related Concept Videos
Catalysis
Routes of Persuasion
Introduction to Mechanisms of Enzyme Catalysis
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Routes of Drug Administration: Parenteral
The intravenous route (IV) of drug administration can be further categorized into two types. The bolus injection administers the entire dose rapidly, while an intravenous infusion slowly delivers smaller doses steadily.
The IV route is often...
Routes of Drug Administration: Overview
Enteral administration refers to drugs absorbed through the gastrointestinal tract. They can be swallowed (perorally), placed under the tongue (sublingually), or on the inner lining of the cheeks (buccally). Perorally administered drugs take time to be absorbed and have a slower onset of action. The rectal route is another form of enteral administration, which allows for...

