Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles.
Akira YOSHIMURA
1
,
Scott C Klasen
1
,
Michael T Shea
1
,
Khiem C Nguyen
1
,
Gregory Rohde
1
,
Akio Saito
2
,
Victor V. Nemykin
1, 4
,
Publication type: Journal Article
Publication date: 2016-12-01
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
27794175
General Chemistry
Catalysis
Organic Chemistry
Abstract
New pseudocyclic benziodoxole tosylates were prepared by the treatment of 1-hydroxybenziodoxolones with p-toluenesulfonic acid or via ligand transfer reaction between PhI(OH)OTs (Koser's reagent) and substituted 2-iodobenzoic acids under mild condition. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.362 Å between oxygen and iodine in the iodoxole ring. Pseudocyclic benziodoxole tosylates readily react with various organic substrates as electrophiles or oxidants to afford the corresponding iodonium salts or the products of oxidation. Furthermore, these compounds can be used as efficient recyclable hypervalent iodine reagents. The reduced form of a pseudocyclic benziodoxole tosylate, 2-iodobenzoic acid, can be efficiently recovered from the reaction mixture by a simple acid-base liquid-liquid biphasic procedure.
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Total citations:
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Citations from 2024:
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MLA
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GOST
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YOSHIMURA A. et al. Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles. // Chemistry - A European Journal. 2016. Vol. 23. No. 3. pp. 691-695.
GOST all authors (up to 50)
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YOSHIMURA A., Klasen S. C., Shea M. T., Nguyen K. C., Rohde G., Saito A., Postnikov P. S., S. Yusubov M., Nemykin V. V., Zhdankin V. V. Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles. // Chemistry - A European Journal. 2016. Vol. 23. No. 3. pp. 691-695.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/chem.201604475
UR - https://doi.org/10.1002/chem.201604475
TI - Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles.
T2 - Chemistry - A European Journal
AU - YOSHIMURA, Akira
AU - Klasen, Scott C
AU - Shea, Michael T
AU - Nguyen, Khiem C
AU - Rohde, Gregory
AU - Saito, Akio
AU - Postnikov, Pavel S.
AU - S. Yusubov, Mekhman
AU - Nemykin, Victor V.
AU - Zhdankin, Viktor V.
PY - 2016
DA - 2016/12/01
PB - Wiley
SP - 691-695
IS - 3
VL - 23
PMID - 27794175
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_YOSHIMURA,
author = {Akira YOSHIMURA and Scott C Klasen and Michael T Shea and Khiem C Nguyen and Gregory Rohde and Akio Saito and Pavel S. Postnikov and Mekhman S. Yusubov and Victor V. Nemykin and Viktor V. Zhdankin},
title = {Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles.},
journal = {Chemistry - A European Journal},
year = {2016},
volume = {23},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/chem.201604475},
number = {3},
pages = {691--695},
doi = {10.1002/chem.201604475}
}
Cite this
MLA
Copy
YOSHIMURA, Akira, et al. “Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles..” Chemistry - A European Journal, vol. 23, no. 3, Dec. 2016, pp. 691-695. https://doi.org/10.1002/chem.201604475.
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