Categories: N-S Bond Formation >
Synthesis of Sulfamates
Related: |
Recent Literature
The combination of calcium triflimide and DABCO activates sulfamoyl fluorides,
fluorosulfates, and sulfonyl fluorides for SuFEx with amines to provide a
diverse set of sulfamides, sulfamates, and sulfonamides at room temperature
under mild conditions.
S. Mahapatra, C. P. Woroch, T. W. Butler, S. N. Carneiro, S. C. Kwan, S. R.
Khasnavis, J. Gu, J. K. Dutra, B. C. Vetelino, J. Bellenger, C. W. am Ende, N.
D. Ball,
Org. Lett., 2020, 22, 4389-4394.
Hexafluoroisopropyl sulfamate is as a bench-stable solid that reacts readily
with a wide variety of alcohols, amines, phenols, and anilines under mild
reaction conditions to provide sulfamates and sulfamides. The sole byproduct of
the reaction is hexafluoroisopropanol and reaction products can often be
isolated in high purity after a simple workup.
M. A. Sguazzin, J. W. Johnson, J. Magolan, Org. Lett., 2021, 23,
3373-3378.
An efficient and operationally simple synthesis of N-acyl sulfamates
from fluorosulfonates and potassium trimethylsilyloxyl imidates as amide
precursor offers broad substrate scope, mild and base-free reaction conditions,
short reaction time, and excellent yields.
S. Zhang, H. Xiong, F. Lu, F. Ma, Y. Gu, P. Ma, H. Xu, G. Yang, J. Org. Chem., 2019, 84,
15380-15388.
In a synthetic strategy toward N-acyl sulfamates, fluorosulfates, a new
emerging class of electrophiles, were used to construct the sulfamate core. The
reaction avoids the handling of sulfamoyl chloride and chlorosulfonyl isocyanate.
In combination with amides, a broad range of N-acyl sulfamates was
synthesized, including functionalized bioactive compounds.
P. Gilles, C. Veryser, S. Vangrunderbeeck, S. Ceusters, L. Van Meervelt, W. M.
De Borggraeve, J. Org. Chem., 2019, 84,
1070-1078.