Download PDF
Synthesis
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.
› Further Information
   Permissions and Reprints All articles of this category


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
  • Supporting Information


Publication History

Received: 13 March 2024

Accepted after revision: 15 April 2024

Article published online:
30 April 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Lee JK, Ahn KC, Park OS, Ko YK. J. Agric. Food Chem. 2002; 50: 1791
      CrossrefPubMed
    • 1b Ma J. Bull. Environ. Contam. Toxicol. 2002; 68: 275
      PubMed
    • 1c Amelin VG, Lavrukhina OI. J. Anal. Chem. 2017; 72: 1
      Crossref
    • 1d Shin Y, Lee J, Lee J, Lee J, Kim E, Liu K, Lee HS, Kim JH. J. Agric. Food Chem. 2018; 66: 3550
      CrossrefPubMed
    • 1e Belakhov VV. Russ. J. Gen. Chem. 2021; 91: 2858
      Crossref
  • 2 Mohammad M, Itoh K, Suyama K. Arch. Environ. Con. Tox. 2010; 58: 605
    CrossrefPubMed
  • 3 Nougadère A, Reninger J, Volatier J, Leblanc J. Food Chem. Toxicol. 2011; 49: 1484
    CrossrefPubMed
    • 4a Picard JA, O’Brien PM, Sliskovic DR, Anderson MK, Bousley RF, Hamelehle KL, Krause BR, Stanfield RL. J. Med. Chem. 1996; 39: 1243
      CrossrefPubMed
    • 4b Mondal S. Comp. Biol. Chem. 2018; 75: 91
      CrossrefPubMed
  • 5 Hirai K, Uchida A, Ohno R. Major Synthetic Routes for Modern Herbicide Classes and Agrochemical Characteristics. In Herbicide Classes in Development: Mode of Action, Targets, Genetic Engineering, Chemistry. Böger P, Wakabayashi K, Hirai K. Springer; Berlin: 2002: 179-289
    CrossrefGoogle Scholar
    • 6a Rasmussen JK, Hassner A. Chem. Rev. 1976; 76: 389
      Crossref
    • 6b Fitzpatrick LJ, Rivero RA. Tetrahedron Lett. 1997; 38: 7479
      Crossref
    • 6c Ulrich H. Chem. Rev. 1965; 65: 369
      Crossref
    • 6d Dhar DN, Dhar P. The Chemistry of Chlorosulfonyl Isocyanate . World Scientific Publishing; Singapore: 2002
      Google Scholar
    • 6e Roesky HW, Hoff A. Chem. Ber. 1968; 101: 162
      Crossref
    • 8a Dong J, Krasnova L, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2014; 53: 9430
      CrossrefPubMed
    • 8b Graf R. Angew. Chem., Int. Ed. Engl. 1968; 7: 172
      Crossref
    • 8c Hoffmann H, Förster H, Tor-Poghossian G. Monatsh. Chem. 1969; 100: 311
      Crossref
  • 9 Sun S, Gao B, Chen J, Sharpless KB, Dong J. Angew. Chem. Int. Ed. 2021; 60: 21195
    CrossrefPubMed
    • 10a Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB. Angew. Chem. Int. Ed. 2005; 44: 3275
      CrossrefPubMed
    • 10b Mahapatra S, Woroch CP, Butler TW, Carneiro SN, Kwan SC, Khasnavis SR, Gu J, Dutra JK, Vetelino BC, Bellenger J, Ende CW, Ball ND. Org. Lett. 2020; 22: 4389
      CrossrefPubMed
    • 11a Appel R, Montenarh M. Chem. Ber. 1977; 110: 2368
      Crossref
    • 11b Atkins GM. Jr, Burgess EM. J. Am. Chem. Soc. 1968; 90: 4744
      Crossref
    • 11c Atkins GM. Jr, Burgess EM. J. Am. Chem. Soc. 1972; 94: 6135
      CrossrefPubMed