Beilstein J. Org. Chem. 2018, 14, 1021–1027.
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on an I(I)/I(III) catalysis manifold. This metal-free fluoro-
cyclisation employs p-iodotoluene (10 mol %) as an inexpen-
sive organocatalyst and Selectfluor® as oxidant. The optimal
amine/HF ratio (1:4.5) is easily obtained by combining com-
mercially available triethylamine tris(hydrogenfluoride)
(Et3N·3HF) and Olah’s reagent (Pyr·HF). Broad functional
group tolerance is observed in the products, the structures of
which display the stereoelectronic fluorine gauche effect.
13.Singh, F. V.; Wirth, T. Catalytic Oxidations with Hypervalent Iodine. In
Catalytic Oxidation in Organic Synthesis; Muñiz, K., Ed.; Science of
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Halides. In Reference Module in Chemistry, Molecular Sciences and
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Supporting Information
Supporting Information File 1
Experimental part.
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19.Quideaux, S.; Wirth, T. Tetrahedron 2010, 66, 5737–5738.
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Acknowledgements
We acknowledge generous financial support from the WWU
Münster and the Deutsche Forschungsgemeinschaft (SFB 858
and Excellence Cluster EXC 1003 “Cells in Motion”). We
thank Dr. Nicola Lucchetti for helpful discussions.
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ORCID® iDs
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See for a discussion of this transformation.
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