Desmethyl SuFEx-IT: SO<sub>2</sub>F<sub>2</sub>-Free Synthesis and Evaluation as a Fluorosulfurylating Agent
Jan Bertram, Felix Neumaier, Boris D. Zlatopolskiy, Bernd Neumaier
Abstract
High Resolution Image Download MS PowerPoint Slide Access to SuFExable compounds was remarkably simplified by introduction of the solid FO 2 S-donor SuFEx-IT. However, the published process for preparation of this reagent relies on the use of sulfuryl fluoride (SO 2 F 2 ), which is difficult to obtain and highly toxic. Herein, we disclose a simple protocol for SO 2 F 2 -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 FO 2 S-donors and enables cost-efficient access to substrates for SuFEx click chemistry.