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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Advancing carbohydrate functionality: The role of hypervalent iodine.

Kapil Upadhyaya1, Sateesh Dubbu2

  • 1Department of Chemical Physiology and Biochemistry, Oregon Health and Science University, Portland, OR 97239, USA.

Carbohydrate Research
|June 12, 2024
PubMed
Summary

Hypervalent iodine reagents offer mild, selective, and stable methods for carbohydrate functionalization. This review highlights their diverse applications in synthesizing complex glycoconjugates and rare sugars.

Keywords:
CH or NH insertion reactionCarbohydratesFunctionalization of glycalsHypervalent iodine

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Hypervalent Iodine Chemistry

Background:

  • Hypervalent iodine reagents have emerged as powerful tools in modern organic synthesis.
  • Their unique properties, including mildness, selectivity, and stability, make them ideal for complex molecule synthesis.
  • Carbohydrate functionalization is crucial for developing new therapeutics and materials.

Purpose of the Study:

  • To review the significant developments and applications of hypervalent iodine reagents in carbohydrate functionalization.
  • To emphasize the versatility of hypervalent iodine compounds in various carbohydrate transformations.
  • To showcase the synthesis of complex glycoconjugates and rare sugars using these reagents.

Main Methods:

  • Glycal functionalization using hypervalent iodine reagents.
  • C-H or N-H insertion reactions mediated by hypervalent iodine compounds.
  • O-arylations, synthesis of C-2 deoxy-2-iodo glycoconjugates, iminosugars, and C3-oxo-glycals.
  • Hypervalent iodine-mediated synthesis of 1,3,5-trioxocanes and rare sugars.

Main Results:

  • Demonstrated successful application of hypervalent iodine reagents in diverse carbohydrate functionalization reactions.
  • Achieved selective synthesis of various complex carbohydrate derivatives, including iminosugars and glycoconjugates.
  • Enabled efficient synthesis of bioactive 1,3,5-trioxocanes and valuable rare sugars.

Conclusions:

  • Hypervalent iodine reagents are highly effective and versatile tools for carbohydrate functionalization.
  • These methods offer mild, selective, and environmentally friendly pathways to valuable carbohydrate structures.
  • The reviewed applications underscore the importance of hypervalent iodine chemistry in advancing carbohydrate science.