2-Iodoxybenzoic Acid Tosylates

the Alternative to Dess–Martin Periodinane Oxidizing Reagents

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4 Citations (Scopus)

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.).

Original languageEnglish
Pages (from-to)3207-3216
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number18
DOIs
Publication statusPublished - 18 Sep 2017

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Carbonyl compounds
Alcohols
Terpenes
Polyketides
Oxidation
Acids
Dehydrogenation
Iodine
Oxidants
Pyridine
Steroids
Temperature
2-iodoxybenzoic acid
pyridine

Keywords

  • alcohols
  • iodine
  • oxidation
  • synthetic methods
  • terpenoids

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents",
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",
author = "Yusubov, {Mekhman S.} and Postnikov, {Pavel S.} and Yusubova, {Roza Ya} and Akira Yoshimura and Gerrit J{\"u}rjens and Andreas Kirschning and Zhdankin, {Viktor V.}",
year = "2017",
month = "9",
day = "18",
doi = "10.1002/adsc.201700776",
language = "English",
volume = "359",
pages = "3207--3216",
journal = "Journal fur Praktische Chemie",
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publisher = "Wiley-VCH Verlag",
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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.

PY - 2017/9/18

Y1 - 2017/9/18

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

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