volume 359 issue 18 pages 3207-3216

2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents

Roza Ya Yusubova 1
Akira YOSHIMURA 1, 2
Gerrit Jürjens 3, 4
Andreas Kirschning 4
Publication typeJournal Article
Publication date2017-09-04
scimago Q1
wos Q1
SJR0.930
CiteScore8.0
Impact factor4.0
ISSN16154150, 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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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.
GOST all authors (up to 50) Copy
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.
RIS |
Cite this
RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
Cite this
MLA Copy
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.