Categories: S-O Bond Formation >
Synthesis of fluorosulfates
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Access to SuFExable compounds was remarkably simplified using the solid FO2S-donor
SuFEx-IT. A hectogram-scale and SO2F2-free preparation of
the analogous desmethyl SuFEx-IT from inexpensive starting materials in high
yield and without chromatographic purification is possible. The use of this
reagent enables the preparation of a series of fluorosulfates and sulfamoyl
fluorides in very high yields.
J. Bertram, F. Neumaier, B. D. Zlatopolskiy, B. Neumaier, J. Org. Chem., 2024, 89,
3821-3833.
Rapid ex situ generation of gaseous sulfuryl fluoride (SO2F2)
from 1,1′-sulfonyldiimidazole as a precursor enables a convenient transformation
of phenols into the corresponding aryl fluorosulfates using a two-chamber
reactor. Various phenols and hydroxylated heteroarenes were fluorosulfated in
good to excellent yields.
C. Veryser, J. Demaerel, V. Bieliu̅nas, P. Gilles, W. M. De Borggraeve, Org. Lett.,
2017, 19, 5244-5247.