2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents
Publication type: Journal Article
Publication date: 2017-09-04
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract
Two powerful hypervalent iodine(V) oxidants, DMP-OTs (1-tosyloxy-1,1-diacetoxy-1H-1λ5-benzo[d][1,2]iodoxol-3-one) and IBX-OTs (1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π-systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX-OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones.
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GOST
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S. Yusubov M. et al. 2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents // Advanced Synthesis and Catalysis. 2017. Vol. 359. No. 18. pp. 3207-3216.
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S. Yusubov M., Postnikov P. S., Yusubova R. Ya., YOSHIMURA A., Jürjens G., Kirschning A., Zhdankin V. V. 2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents // Advanced Synthesis and Catalysis. 2017. Vol. 359. No. 18. pp. 3207-3216.
Cite this
RIS
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TY - JOUR
DO - 10.1002/adsc.201700776
UR - https://doi.org/10.1002/adsc.201700776
TI - 2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents
T2 - Advanced Synthesis and Catalysis
AU - S. Yusubov, Mekhman
AU - Postnikov, Pavel S.
AU - Yusubova, Roza Ya
AU - YOSHIMURA, Akira
AU - Jürjens, Gerrit
AU - Kirschning, Andreas
AU - Zhdankin, Viktor V.
PY - 2017
DA - 2017/09/04
PB - Wiley
SP - 3207-3216
IS - 18
VL - 359
SN - 1615-4150
SN - 1615-4169
ER -
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BibTex (up to 50 authors)
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@article{2017_S. Yusubov,
author = {Mekhman S. Yusubov and Pavel S. Postnikov and Roza Ya Yusubova and Akira YOSHIMURA and Gerrit Jürjens and Andreas Kirschning and Viktor V. Zhdankin},
title = {2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents},
journal = {Advanced Synthesis and Catalysis},
year = {2017},
volume = {359},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/adsc.201700776},
number = {18},
pages = {3207--3216},
doi = {10.1002/adsc.201700776}
}
Cite this
MLA
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S. Yusubov, Mekhman, et al. “2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents.” Advanced Synthesis and Catalysis, vol. 359, no. 18, Sep. 2017, pp. 3207-3216. https://doi.org/10.1002/adsc.201700776.
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