Categories: S-O Bond Formation >
Synthesis of sulfamates
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Recent Literature
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.
N-Methylimidazole catalyzes alcohol sulfamoylation using
electron-deficient aryl sulfamates as activated group transfer reagents under
mild conditions. The reaction provides intrinsic selectivity for 1° over 2°
alcohols. The requisite aryl sulfamate donors are stable crystalline solids that
can be readily prepared on a large scale.
P. B. Rapp, K. Murai, N. Ichiishi, D. K. Leahy, S. J. Miller,
Org. Lett., 2020, 22, 168-174.