Sulfonylimino Group Transfer Reaction Using Imino-λ³-iodanes with I₂ as Catalyst Under Metal-free Conditions

Akira Yoshimura, Cody L. Makitalo, Melissa E. Jarvi, Michael T. Shea, Pavel S. Postnikov, Gregory T. Rohde, Viktor Zhdankin, Akio Saito, Mekhman S. Yusubov

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


A new practical procedure of imination for sulfide has been developed. The treatment of ( N-tosylimino)-phenyl-λ³-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I₂ under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with moderate to good yields. This facile transfer procedure of the sulfonylimino group can also be applied to triphenylphosphine to produce the respective iminotriphenylphosphoranes in high yields. According to the reaction mechanism studies, the process of imination from ( N-tosylimino)-phenyl-λ³-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.

Original languageEnglish (US)
Article number979
Issue number5
StatePublished - Mar 11 2019

Bibliographical note

Funding Information:
Funding: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081 and RSF-19-13-00011) and the Tomsk Polytechnic University Competitiveness Enhancement Program. A.S. is also thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199).

Publisher Copyright:
© 2019 by the authors.


  • Amidyl radical
  • Catalytic cycle
  • Imination
  • Iminoiodanes
  • Iminophosphorane
  • Iodine
  • Phosphine
  • Sulfide
  • Sulfilimine
  • Metals/chemistry
  • Sulfides/chemistry
  • Imines/chemistry
  • Catalysis
  • Iodine/chemistry

PubMed: MeSH publication types

  • Journal Article


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