Tagged hypervalent iodine reagents: A new purification concept based on ion exchange through SN2 substitution

Eike Kunst, Florian Gallier, Gilles Dujardin, Mekhman S. Yusubov, Andreas Kirschning

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

(Chemical Equation Presented) The preparation of phenylsulfonate-tagged iodine(III) reagents as well as their use in a novel purification strategy for iodine(III)-promoted reactions is described. The concept is based on ion exchange and is initiated by an azide-promoted SN2-reaction at the alkyl sulfonate followed by trapping of the resulting aryl sulfonate anion with an ion-exchange resin. The concept is successfully proven for Ru-catalyzed oxidations of alcohols, the activation and glycosidatlon of thioglycosides, and the Suárez reaction of pyranoses.

Original languageEnglish
Pages (from-to)5199-5202
Number of pages4
JournalOrganic Letters
Volume9
Issue number25
DOIs
Publication statusPublished - 6 Dec 2007

Fingerprint

Ion Exchange
purification
Iodine
Arylsulfonates
iodine
Purification
reagents
Ion exchange
Alkanesulfonates
Substitution reactions
Thioglycosides
substitutes
Ion Exchange Resins
sulfonates
Azides
ion exchange resins
Anions
ions
Chemical activation
Alcohols

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Tagged hypervalent iodine reagents : A new purification concept based on ion exchange through SN2 substitution. / Kunst, Eike; Gallier, Florian; Dujardin, Gilles; Yusubov, Mekhman S.; Kirschning, Andreas.

In: Organic Letters, Vol. 9, No. 25, 06.12.2007, p. 5199-5202.

Research output: Contribution to journalArticle

Kunst, Eike ; Gallier, Florian ; Dujardin, Gilles ; Yusubov, Mekhman S. ; Kirschning, Andreas. / Tagged hypervalent iodine reagents : A new purification concept based on ion exchange through SN2 substitution. In: Organic Letters. 2007 ; Vol. 9, No. 25. pp. 5199-5202.
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