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Related Concept Videos

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

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As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
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Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

24.0K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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Cu-Catalyzed Decarboxylative Borylation.

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  • 1Department of Chemistry, The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, California 92037, United States.

ACS Catalysis
|December 4, 2018
PubMed
Summary
This summary is machine-generated.

Researchers developed a straightforward copper-catalyzed method to convert carboxylic acids into boronic esters using redox-active esters (RAEs). This inexpensive and rapid technique offers a simpler alternative to existing protocols for synthesizing valuable boronic ester compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carboxylic acids are versatile starting materials in organic synthesis.
  • Boronic esters are important intermediates in various chemical transformations, including cross-coupling reactions.
  • Existing methods for converting carboxylic acids to boronic esters can be complex, costly, or time-consuming.

Purpose of the Study:

  • To develop a simple, efficient, and cost-effective method for synthesizing boronic esters from carboxylic acids.
  • To utilize copper catalysis and redox-active esters (RAEs) for this transformation.
  • To explore the scope and limitations of the new synthetic route.

Main Methods:

  • Copper-catalyzed conversion of carboxylic acids to boronic esters.
  • Utilized redox-active esters (RAEs) as key intermediates.
  • Investigated the reaction scope with various carboxylic acid substrates.
  • Performed kinetic studies to understand reaction mechanisms and dependencies.

Main Results:

  • A broad scope of carboxylic acids was successfully converted to boronic esters.
  • The developed method is operationally simple, rapid, and inexpensive compared to existing protocols.
  • Kinetic analysis provided insights into substrate and reagent concentration effects.

Conclusions:

  • The reported copper-catalyzed method offers a highly practical and efficient route to boronic esters from carboxylic acids.
  • This approach represents a significant advancement in synthetic methodology, providing an accessible tool for chemists.
  • The findings facilitate the broader application of boronic esters in organic synthesis.