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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Boronic acid catalysis.

Dennis G Hall1

  • 1Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada. dennis.hall@ualberta.ca.

Chemical Society Reviews
|May 16, 2019
PubMed
Summary
This summary is machine-generated.

Boronic acid catalysis (BAC) offers a mild method to activate hydroxy groups, enabling diverse organic reactions like amide formation and Friedel-Crafts alkylations. This approach enhances reaction efficiency and selectivity, avoiding harsh reagents.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Boronic acids are primarily known as reagents in transition metal catalysis.
  • Emerging applications highlight their potential as reaction catalysts.
  • Limited methods exist for mild catalytic activation of hydroxy functional groups.

Purpose of the Study:

  • To explore the catalytic potential of boronic acids for activating hydroxy groups.
  • To demonstrate the utility of boronic acid catalysis (BAC) in various organic transformations.
  • To showcase BAC's ability to promote reactions under mild and selective conditions.

Main Methods:

  • Utilizing the reversible covalent bonding of boronic acids with hydroxyl groups.
  • Employing boronic acids for both electrophilic and nucleophilic activation modes.
  • Applying BAC to reactions involving carboxylic acids, alcohols, diols, and saccharides.

Main Results:

  • BAC enables electrophilic activation of carboxylic acids for amide formation and conjugate additions.
  • Boronic acid catalysts activate alcohols to form carbocation intermediates for Friedel-Crafts-type reactions.
  • Tetrahedral adducts formed with diols and saccharides enhance their nucleophilicity.

Conclusions:

  • Boronic acid catalysis (BAC) provides a versatile and mild strategy for activating hydroxy functional groups.
  • BAC facilitates diverse organic reactions with high selectivity and atom economy.
  • This catalytic approach circumvents the need for traditional, wasteful stoichiometric activation methods.