Synthesis and Evaluation of Fluorous-Tagged and Polystyrene-Supported Precursors for Fluoro-benziodoxole

Léanne Racicot; John F. Valliant; Graham K. Murphy

doi:10.1055/a-2085-3284

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(17): 2730-2736
DOI: 10.1055/a-2085-3284

paper

Synthesis and Evaluation of Fluorous-Tagged and Polystyrene-Supported Precursors for Fluoro-benziodoxole

Léanne Racicot

^aDepartment of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, Ontario, Canada, N2L 3G1, Canada

^bDepartment of Chemistry and Biochemistry, McMaster University, 1280 Main St. West, Hamilton, Ontario, Canada, L8S 4M3, Canada

,

John F. Valliant ∗

^bDepartment of Chemistry and Biochemistry, McMaster University, 1280 Main St. West, Hamilton, Ontario, Canada, L8S 4M3, Canada

,

Graham K. Murphy ∗

^aDepartment of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, Ontario, Canada, N2L 3G1, Canada

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Abstract

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Abstract

Fluoro-benziodoxole, a fluorinated hypervalent iodine (HVI) reagent, has been prepared by fluoride exchange with fluorous- or polystyrene-based sulfonyloxy-benziodoxole precursors. Key to this strategy was the facile O-sulfonylation of a common hydroxy-benziodoxole precursor with sulfonyl chlorides, which enabled the easy synthesis and evaluation of previously unknown fluorous- or polystyrene-based fluoride exchange precursors. Fluorination of a fluorous-tagged iodane led to fluoro-benziodoxole in 67% yield in 10 minutes with TBAF, whereas fluoride exchange on the polystyrene-supported iodane led to the fluoro-benziodoxole in 82 ± 5% yield upon reacting with TBAF for 10 minutes.

Key words

hypervalent iodine - fluorination - fluorous - solid-supported synthesis - synthetic methodology - radiofluorination

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Referenzen

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Zusatzmaterial

Supporting Information