Tagged hypervalent iodine reagents: a new purification concept based on ion exchange through SN2 substitution.
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 glycosidation of thioglycosides, and the SuArez reaction of pyranoses.
Kunst
Eike
E
Institut für Organische Chemie der Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
Gallier
Florian
F
Dujardin
Gilles
G
Yusubov
Mekhman S
MS
Kirschning
Andreas
A
D000097:Acetonitriles / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D000476:Alkanesulfonates / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D017613:Iodine Compounds / Q000737:chemistry* / Q000302:isolation & purification*; D007474:Ion Exchange; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000097:Acetonitriles; D000438:Alcohols; D000476:Alkanesulfonates; D006027:Glycosides; D017613:Iodine Compounds; C032159:acetonitrile