Details
| Original language | English |
|---|---|
| Pages (from-to) | 3207-3216 |
| Number of pages | 10 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 18 |
| Publication status | Published - 14 Jul 2017 |
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. (Figure presented.).
Keywords
- alcohols, iodine, oxidation, synthetic methods, terpenoids
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Advanced Synthesis and Catalysis, Vol. 359, No. 18, 14.07.2017, p. 3207-3216.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - 2-Iodoxybenzoic Acid Tosylates
T2 - the Alternative to Dess–Martin Periodinane Oxidizing Reagents
AU - Yusubov, Mekhman S.
AU - Postnikov, Pavel S.
AU - Yusubova, Roza Ya
AU - Yoshimura, Akira
AU - Jürjens, Gerrit
AU - Kirschning, Andreas
AU - Zhdankin, Viktor V.
N1 - Funding information: This work was supported by research grants from the Russian Science Foundation (RSF-16-13-10081) and the National Science Foundation (CHE-1262479).
PY - 2017/7/14
Y1 - 2017/7/14
N2 - 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. (Figure presented.).
AB - 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. (Figure presented.).
KW - alcohols
KW - iodine
KW - oxidation
KW - synthetic methods
KW - terpenoids
UR - http://www.scopus.com/inward/record.url?scp=85028727130&partnerID=8YFLogxK
U2 - 10.1002/adsc.201700776
DO - 10.1002/adsc.201700776
M3 - Article
AN - SCOPUS:85028727130
VL - 359
SP - 3207
EP - 3216
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 18
ER -