Categories: N-S Bond Formation >
Synthesis of Sulfamates
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.