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Synthesis 2024; 56(13): 2136-2144
DOI: 10.1055/s-0043-1774860
paper

Hexafluoroisopropyl N-Fluorosulfonyl Carbamate: Synthesis and Its Facile Transformation to Sulfamoyl Ureas

Shuo Liu‡
a   Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
b   School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Xixi Li‡
c   Laboratory of Organofluorine Chemistry Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200232, P. R. of China
,
Xiaolei Wang
a   Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
b   School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Long Xu  ∗
a   Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Jiajia Dong∗
a   Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
b   School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
d   Shanghai Artificial Intelligence Laboratory, Shanghai, 200232, P. R. of China
› Author AffiliationsThe authors acknowledge the Ministry of Science and Technology of China, Major State Basic Research Development Program of China (2021YFF0701704), Shanghai Pilot Program for Basic Research (21TQ1400223), and Shanghai Jiao Tong University for financial support.
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Abstract

The synthesis of hexafluoroisopropyl N-fluorosulfonyl carbamate (HFC) and its facile transformation to sulfamoyl ureas are reported . Unlike liquid chlorosulfonyl isocyanate (CSI) and fluorosulfonyl isocyanate (FSI), which are corrosive and moisture-sensitive, HFC is a white solid and displays satisfactory bench-stability and unique reactivity, which facilitates its double ligation with amines to directly afford a series of sulfamoyl ureas under ambient conditions. It is worth noting that HFC will serve as an efficient surrogate to CSI and FSI for laboratory use, especially for accessing the bioactive sulfamoyl ureas under mild conditions.

Keywords

sulfamoyl ureas - reagent - hexafluoroisopropanol - bench-stability - DABCO

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1774860
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Publication History

Received: 13 March 2024

Accepted after revision: 15 April 2024

Article published online:
30 April 2024

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