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Videos de Conceptos Relacionados

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Amines to Alkenes: Cope Elimination01:14

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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

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Eliminación reductiva lenta de los complejos de amido madre del arilpaladio.

Jessica L Klinkenberg1, John F Hartwig

  • 1Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|August 11, 2010
PubMed
Resumen

Este estudio revela que los complejos de paladio con ligandos voluminosos específicos facilitan la eliminación reductiva de las arylaminas primarias, desafiando las tendencias anteriores en química organometálica y catálisis.

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Área de la Ciencia:

  • Química organometálica Química orgánica de los metales.
  • La catálisis de la catálisis.
  • Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

  • La eliminación reductiva es un paso clave en muchos ciclos catalíticos, pero su eficiencia está influenciada por las propiedades del ligando y el sustrato.
  • Los complejos de paladio son catalizadores ampliamente utilizados en reacciones de acoplamiento cruzado, incluida la formación de enlaces C-N.

Objetivo del estudio:

  • Para investigar la eliminación reductiva de las arylaminas primarias de arylpalladium (II) complejos de amido madre.
  • Comprender la influencia de los ligandos de bisfosfina en la formación, estabilidad y reactividad de estos complejos.

Principales métodos:

  • Síntesis y caracterización de los complejos de amido progenitor de arilpaladio ligado a la bisfosfina (II).
  • Estudios cinéticos de las reacciones de eliminación reductora.
  • Estudios computacionales (por ejemplo, DFT) para dilucidar los mecanismos de reacción y los efectos estéricos.

Principales resultados:

  • Los complejos de amido madre de arylpalladium ligados por la alquilbisfosfina forman CyPF-t-Bu y se someten a una eliminación reductora, a diferencia de los que tienen bisfosfinas aromáticas (DPPF, BINAP).
  • Los complejos ligados con CyPF-t-Bu exhiben tasas de eliminación reductoras más lentas en comparación con los análogos de arylamido o alquilamido, a pesar de la basicidad del ligando amido padre.
  • Los complejos de amido madre muestran una formación más rápida y una mayor estabilidad termodinámica que los complejos de arylamido.
  • Los efectos estéricos, apoyados por estudios computacionales, juegan un papel dominante en la estabilidad y la reactividad de estos complejos.

Conclusiones:

  • El voluminoso ligando de alquilbisfosfina CyPF-t-Bu estabiliza el complejo de amido de arilpaladio, lo que lo convierte en el estado de reposo en el acoplamiento de haluro de arilo con amoníaco.
  • Este hallazgo contrasta con las típicas reacciones de aminación catalizadas por paladio donde las especies Pd(0) o arylpalladium(II) son a menudo los estados de reposo.
  • La influencia estérica de los ligandos es crucial para controlar la reactividad en las reacciones de aminación catalizadas por el paladio.