Imino-λ3-iodane and Catalytic Amount of I2-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement

Cody L. Makitalo; Akira Yoshimura; Gregory T. Rohde; Irina A. Mironova; Rosa Y. Yusubova; Mekhman S. Yusubov; Viktor V. Zhdankin; Akio Saito

doi:10.1002/ejoc.202000961

Imino-λ³-iodane and Catalytic Amount of I₂-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement

Cody L. Makitalo, Akira Yoshimura, Gregory T. Rohde, Irina A. Mironova, Rosa Y. Yusubova, Mekhman S. Yusubov, Viktor V. Zhdankin, Akio Saito

Chemistry & Biochemistry

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

5 Scopus citations

Abstract

A facile metal-free [2,3]-sigmatropic rearrangement reaction of allyl sulfides via N-sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino-λ³-iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N-allylsulfenamide compounds in moderate to good yields. Several N-allylsulfenamide structures have been confirmed by single-crystal X-ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino-λ³-iodane and the sulfur atom, resulting in the formation of N-sulfilimine species, followed by [2,3]-sigmatropic rearrangement to form the N-allylsulfenamide.

Original language	English (US)
Pages (from-to)	6433-6439
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	41
DOIs	https://doi.org/10.1002/ejoc.202000961
State	Published - Nov 8 2020

Bibliographical note

Funding Information:
This work was supported by a research grants from the Russian Science Foundation (RSF‐16‐13‐10081‐P) and the National Science Foundation (CHE‐1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). Some research was carried out using the core facilities of TPU's “Physical and chemical methods of analysis”.

Keywords

Hypervalent compounds
Iodine
Sigmatropic rearrangement
Sulfilimines
Synthetic methods

Publisher link

10.1002/ejoc.202000961

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@article{7e772702bcda41668781867268c1a212,

title = "Imino-λ3-iodane and Catalytic Amount of I2-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement",

abstract = "A facile metal-free [2,3]-sigmatropic rearrangement reaction of allyl sulfides via N-sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino-λ3-iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N-allylsulfenamide compounds in moderate to good yields. Several N-allylsulfenamide structures have been confirmed by single-crystal X-ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino-λ3-iodane and the sulfur atom, resulting in the formation of N-sulfilimine species, followed by [2,3]-sigmatropic rearrangement to form the N-allylsulfenamide.",

keywords = "Hypervalent compounds, Iodine, Sigmatropic rearrangement, Sulfilimines, Synthetic methods",

author = "Makitalo, {Cody L.} and Akira Yoshimura and Rohde, {Gregory T.} and Mironova, {Irina A.} and Yusubova, {Rosa Y.} and Yusubov, {Mekhman S.} and Zhdankin, {Viktor V.} and Akio Saito",

note = "Funding Information: This work was supported by a research grants from the Russian Science Foundation (RSF‐16‐13‐10081‐P) and the National Science Foundation (CHE‐1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). Some research was carried out using the core facilities of TPU's “Physical and chemical methods of analysis”.",

year = "2020",

month = nov,

day = "8",

doi = "10.1002/ejoc.202000961",

language = "English (US)",

volume = "2020",

pages = "6433--6439",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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T1 - Imino-λ3-iodane and Catalytic Amount of I2-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement

AU - Makitalo, Cody L.

AU - Yoshimura, Akira

AU - Rohde, Gregory T.

AU - Mironova, Irina A.

AU - Yusubova, Rosa Y.

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor V.

AU - Saito, Akio

N1 - Funding Information: This work was supported by a research grants from the Russian Science Foundation (RSF‐16‐13‐10081‐P) and the National Science Foundation (CHE‐1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). Some research was carried out using the core facilities of TPU's “Physical and chemical methods of analysis”.

PY - 2020/11/8

Y1 - 2020/11/8

N2 - A facile metal-free [2,3]-sigmatropic rearrangement reaction of allyl sulfides via N-sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino-λ3-iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N-allylsulfenamide compounds in moderate to good yields. Several N-allylsulfenamide structures have been confirmed by single-crystal X-ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino-λ3-iodane and the sulfur atom, resulting in the formation of N-sulfilimine species, followed by [2,3]-sigmatropic rearrangement to form the N-allylsulfenamide.

AB - A facile metal-free [2,3]-sigmatropic rearrangement reaction of allyl sulfides via N-sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino-λ3-iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N-allylsulfenamide compounds in moderate to good yields. Several N-allylsulfenamide structures have been confirmed by single-crystal X-ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino-λ3-iodane and the sulfur atom, resulting in the formation of N-sulfilimine species, followed by [2,3]-sigmatropic rearrangement to form the N-allylsulfenamide.

KW - Hypervalent compounds

KW - Iodine

KW - Sigmatropic rearrangement

KW - Sulfilimines

KW - Synthetic methods

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