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 V. Zhdankin,
Akio Saito,
Mekhman S. Yusubov
Affiliations
Akira Yoshimura
Research School of Chemistry and Applied Biomedical Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russia
Cody L. Makitalo
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Melissa E. Jarvi
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Michael T. Shea
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Pavel S. Postnikov
Research School of Chemistry and Applied Biomedical Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russia
Gregory T. Rohde
Marshall School, Duluth, MN 55811, USA
Viktor V. Zhdankin
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Akio Saito
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
Mekhman S. Yusubov
Research School of Chemistry and Applied Biomedical Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russia
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.
