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Videos de Conceptos Relacionados

Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.3K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.0K
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...
9.0K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.2K
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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Gyroid Nickel Nanostructures from Diblock Copolymer Supramolecules
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Catalización por níquel de las amidas de alquenilo simples

Joseph Derosa1, Roman Kleinmans1, Van T Tran1

  • 1Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.

Journal of the American Chemical Society
|December 12, 2018
PubMed
Resumen

Este estudio introduce una nueva reacción catalizada por níquel para crear productos 1,2-diarilados a partir de amidas simples y compuestos de arilo. El método utiliza un ligando de olefinas con deficiencia de electrones para un excelente control regional en la síntesis orgánica.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Las reacciones de acoplamiento son vitales en la síntesis orgánica.
  • El desarrollo de métodos regioselectivos para la síntesis de moléculas complejas sigue siendo un desafío.
  • Los grupos funcionales de amida pueden ser difíciles de dirigir en la catálisis.

Objetivo del estudio:

  • Para reportar una nueva reacción de acoplamiento cruzado con catalizar el níquel.
  • Para lograr la diarilación regionalizada de las amidas de alquenilo.
  • Explorar la utilidad de los ligandos olefinos con deficiencia de electrones en el acoplamiento cruzado.

Principales métodos:

  • La reacción de acoplamiento cruzado catalizada por níquel.
  • Se utilizaron amidas de alquenilo simples, yoduros de arilo y ésteres de boro de arilo.
  • Se utiliza el fumarato de dimetilo como un ligando de olefinas con deficiencia de electrones (EDO).
  • Condiciones de reacción optimizadas para el rendimiento y la regioselectividad.

Principales resultados:

  • Se han sintetizado con éxito productos 1,2-diarilados con un excelente control regional.
  • Compatibilidad demostrada con una amplia gama de amidas derivadas del ácido 3-butenoico, el ácido 4-pentenoico y la amina alila.
  • Se trata de la primera diarilación controlada regionalizada dirigida por un grupo de amida nativo.
  • El análisis computacional proporcionó información sobre el mecanismo de reacción y el papel del ligando.

Conclusiones:

  • Desarrolló un método nuevo y eficiente para la diarilación de 1,2-región controlada.
  • El uso de ligandos EDO es crucial para el éxito de la reacción.
  • Esta metodología amplía el alcance de las reacciones de acoplamiento cruzado dirigidas por amida.