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Synthesis of N-Acyl Sulfamates from Fluorosulfates and Amides

Philippe Gilles, Cedrick Veryser, Sarah Vangrunderbeeck, Sam Ceusters, Luc Van Meervelt, Wim M. De Borggraeve*

*Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Box 2404, 3001 Leuven, Belgium, Email:

P. Gilles, C. Veryser, S. Vangrunderbeeck, S. Ceusters, L. Van Meervelt, W. M. De Borggraeve, J. Org. Chem., 2019, 84, 1070-1078.

DOI: 10.1021/acs.joc.8b02785

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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.

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Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

C. Veryser, J. Demaerel, V. Bieliu̅nas, P. Gilles, W. M. De Borggraeve, Org. Lett., 2017, 19, 5244-5247.

Key Words


ID: J42-Y2019