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

doi:10.3390/molecules24050979

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

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.

Original language	English (US)
Article number	979
Journal	Molecules
Volume	24
Issue number	5
DOIs	https://doi.org/10.3390/molecules24050979
State	Published - 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.

Keywords

Amidyl radical
Catalytic cycle
Imination
Iminoiodanes
Iminophosphorane
Iodine
Phosphine
Sulfide
Sulfilimine

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title = "Sulfonylimino group transfer reaction using imino-λ3-iodanes with I2 as catalyst under metal-free conditions",

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.",

keywords = "Amidyl radical, Catalytic cycle, Imination, Iminoiodanes, Iminophosphorane, Iodine, Phosphine, Sulfide, Sulfilimine",

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

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: {\textcopyright} 2019 by the authors.",

year = "2019",

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AU - Yoshimura, Akira

AU - Makitalo, Cody L.

AU - Jarvi, Melissa E.

AU - Shea, Michael T.

AU - Postnikov, Pavel S.

AU - Rohde, Gregory T.

AU - Zhdankin, Viktor

AU - Saito, Akio

AU - Yusubov, Mekhman S.

N1 - 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.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

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KW - Phosphine

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KW - Sulfilimine

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