Sulfonylimino group transfer reaction using imino-λ 3 -iodanes with I 2 as catalyst under metal-free conditions

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

Research output: Contribution to journalArticle

Abstract

A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-λ 3 -iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I 2 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-λ 3 -iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.

Original languageEnglish
Article number979
JournalMolecules
Volume24
Issue number5
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • Amidyl radical
  • Catalytic cycle
  • Imination
  • Iminoiodanes
  • Iminophosphorane
  • Iodine
  • Phosphine
  • Sulfide
  • Sulfilimine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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