TY  - JOUR
AU  - Bertram, Jan
AU  - Neumaier, Felix
AU  - Zlatopolskiy, Boris
AU  - Neumaier, Bernd
TI  - Desmethyl SuFEx-IT: SO2F2 - Free Synthesis and Evaluation as a Fluorosulfurylating Agent
JO  - The journal of organic chemistry
VL  - 89
IS  - 6
SN  - 0022-3263
CY  - [Erscheinungsort nicht ermittelbar]
PB  - American Chemical Society
M1  - FZJ-2024-01796
SP  - 3821-3833
PY  - 2024
AB  - 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.
LB  - PUB:(DE-HGF)16
C6  - 38386004
UR  - <Go to ISI:>//WOS:001174376900001
DO  - DOI:10.1021/acs.joc.3c02643
UR  - https://juser.fz-juelich.de/record/1023777
ER  -