Next Article in Journal
Tea Seed Oil Prevents Obesity, Reduces Physical Fatigue, and Improves Exercise Performance in High-Fat-Diet-Induced Obese Ovariectomized Mice
Next Article in Special Issue
Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
Previous Article in Journal
Chemicals from Food Supply Chain By-Products and Waste Streams
Article Menu
Issue 5 (March-1) cover image

Export Article

Open AccessArticle
Molecules 2019, 24(5), 979; https://doi.org/10.3390/molecules24050979

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

1
Research School of Chemistry and Applied Biomedical Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russia
2
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
3
Marshall School, Duluth, MN 55811, USA
4
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Kazunori Miyamoto
Received: 13 February 2019 / Revised: 5 March 2019 / Accepted: 7 March 2019 / Published: 11 March 2019
(This article belongs to the Special Issue Advances in the Chemistry of Hypervalent Iodine Compounds)
Full-Text   |   PDF [1989 KB, uploaded 11 March 2019]   |  

Abstract

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. View Full-Text
Keywords: iminoiodanes; imination; sulfide; sulfilimine; phosphine; iminophosphorane; amidyl radical; catalytic cycle; iodine iminoiodanes; imination; sulfide; sulfilimine; phosphine; iminophosphorane; amidyl radical; catalytic cycle; iodine
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Yoshimura, A.; Makitalo, C.L.; Jarvi, M.E.; Shea, M.T.; Postnikov, P.S.; Rohde, G.T.; Zhdankin, V.V.; Saito, A.; Yusubov, M.S. Sulfonylimino Group Transfer Reaction Using Imino-λ3-iodanes with I2 as Catalyst Under Metal-free Conditions. Molecules 2019, 24, 979.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top