Categories: S-O Bond Formation >
Synthesis of sulfamates
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.