Hypervalent Iodine Compounds in Carbohydrate Chemistry: Glycosylation, Functionalization and Oxidation

Abstract

This mini review article provides an overview on the use of hypervalent iodine compounds (HICs) in carbohydrate synthesis, focusing on their chemistry and recent applications. HICs are similar to transition metals in their reactivity but have the added benefit of being environmentally benign, and are therefore commonly used as selective oxidants and eco‐friendly reagents in organic synthesis. Herein, we summarize various synthetic uses of hypervalent iodine reagents in reactions such as glycosylation, oxidations, functionalization, and C−C bond‐forming reactions. The goal of this review is to illustrate the advantages and versatility of using HICs as an environmentally sustainable alternative to heavy metals in carbohydrate chemistry.

Iodosylbenzene-Promoted Glycosylation with Selenoglycosides: Application in One-Pot Glycosylation

“…In particular, organic hypervalent iodine compounds are widely used as oxidizing reagents in organic synthesis, which are easy to prepare, mild, and environmentally friendly . Due to their excellent thiophilicity and selenophilicity, hypervalent iodine reagents are increasingly used in activating thioglycoside donors. − We intended to find a hypervalent iodine reagent that can efficiently activate selenoglycosides while ensuring the stability of thioglycosides and screened a series of trivalent iodine reagents (see Figure S1 for compound structures) to activate selenoglycosides.…”