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

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

Publication History

Received: 28 March 2023

Accepted: 03 May 2023

Accepted Manuscript online:
03 May 2023

Article published online:
24 May 2023

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