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- W4313408308 abstract "Abstract A regioselective fluorocyclisation of β,γ‐unsaturated oximes through I(I)/I(III) catalysis is disclosed to generate 5‐fluoromethylated isoxazolines. The transformation leverages p ‐iodotoluene as an inexpensive catalyst, Selectfluor ® as the terminal oxidant and an amine⋅HF complex (1 : 7.5) as both the fluoride and Brønsted acid source. The λ 3 ‐iodane p ‐TolIF 2 , which is generated in situ , engages the pendant alkene of the substrate to facilitate a cyclisation/fluorination sequence. A range of 5‐fluoromethyl isoxazolines can be generated using this method, including aliphatic and aromatic systems (up to 56 % yield). Single crystal X‐ray analysis of a representative example reveals a conformation that is consistent with the stereoelectronic gauche effect between the exocyclic C(sp 3 )−F bond and the C(sp 3 )−O of the isoxazoline (ϕ OCCF =−62.0°)." @default.
- W4313408308 created "2023-01-06" @default.
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- W4313408308 date "2023-02-03" @default.
- W4313408308 modified "2023-09-25" @default.
- W4313408308 title "Fluorocyclisation of Oximes to Isoxazolines Through I(I)/I(III) Catalysis" @default.
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- W4313408308 doi "https://doi.org/10.1002/hlca.202200183" @default.
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