Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines.

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 (σ_C-C→σ*_C-F and σ_C-H→σ*_C-O). This manifestation of the stereoelectronic gauche effect was established by X-ray crystallographic analysis of a representativ

SUBMITTER: Scheidt F 

PROVIDER: S-EPMC6009682 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature