Journal Article

FZJ-2024-01796

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Desmethyl SuFEx-IT: SO2F2 - Free Synthesis and Evaluation as a Fluorosulfurylating Agent

Bertram, J.FZJ* ; Neumaier, F.FZJ* ; Zlatopolskiy, B.FZJ* ; Neumaier, B. (Corresponding author)FZJ*

2024
American Chemical Society [Erscheinungsort nicht ermittelbar]

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Please use a persistent id in citations: doi:10.1021/acs.joc.3c02643  doi:10.34734/FZJ-2024-01796

Abstract: Access to SuFExable compounds was remarkably simplified by introduction of the solid FO2S-donor SuFEx-IT. However, the published process for preparation of this reagent relies on the use of sulfuryl fluoride (SO2F2), which is difficult to obtain and highly toxic. Herein, we disclose a simple protocol for SO2F2-free, hectogram-scale preparation of the analogous desmethyl SuFEx-IT from inexpensive starting materials. The reagent was prepared in a high (85%) total yield and without chromatographic purification steps. In addition, we demonstrate the utility of desmethyl SuFEx-IT by successful preparation of a series of fluorosulfates and sulfamoyl fluorides in high to excellent yields. As such, our work recognizes desmethyl SuFEx-IT as a valuable alternative to common FO2Sdonors and enables cost-efficient access to substrates for SuFEx click chemistry.

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Contributing Institute(s):

1. Nuklearchemie (INM-5)

Research Program(s):

1. 5253 - Neuroimaging (POF4-525) (POF4-525)

Appears in the scientific report 2024

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