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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

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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,...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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α-Alkylation of Ketones via Enolate Ions01:10

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Alquilarización regioselectiva Ni-Catalizada de Alquenos No Activados en Aminas Habilitada por Efectos Cooperativos

Vivek Aryal1, Supuni I N Hewa Inaththappulige1, Ayush Acharya1

  • 1Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.

Journal of the American Chemical Society
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Este estudio introduce una nueva reacción catalizada por níquel para la alquilarización de alquenos utilizando aminas. El método crea eficientemente valiosas δ- y ε-arilaminas con ramificación, expandiendo las posibilidades sintéticas.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • El desarrollo de métodos eficientes para la formación de enlaces C-C es crucial en la síntesis orgánica.
  • La alquilación y la arilación de alquenos no activados siguen siendo transformaciones sintéticas desafiantes.
  • Las moléculas que contienen aminas prevalecen en productos farmacéuticos y naturales.

Objetivo del estudio:

  • Desarrollar una nueva alquilación vicinal catalizada por níquel de alquenos no activados en alquenilaminas.
  • Para permitir la síntesis de las arilaminas δ y ε ramificadas utilizando materiales de partida fácilmente disponibles.
  • Explorar el alcance y las limitaciones del sistema catalítico desarrollado.

Principales métodos:

  • Reacción de acoplamiento catalizada por níquel utilizando haluros de arilo y reactivos de alquilzinco.
  • Utilizando las γ,δ- y δ,ε-alquenilaminas como sustratos, que incluyen aminas primarias, secundarias y terciarias.
  • Investigar el mecanismo de reacción a través de estudios mecanicistas, incluida la función de los ligandos.

Principales resultados:

  • Alquilarización vicinal exitosa de alquenos no activados en las alquenilaminas.
  • Formación de dos nuevos enlaces C ((sp3) - C ((sp3) y C ((sp3) - C ((sp2).
  • Síntesis de diversas δ- y ε-arilaminas con ramificación C(sp3) en las posiciones γ y δ, utilizando varios yoduros de arilo/heteroarilo y reactivos de alquilzinco.

Conclusiones:

  • Se ha establecido un nuevo método catalizado por Ni para la alquilarización vicinal de las alquenilaminas.
  • La reacción demuestra un amplio alcance del sustrato, tolerando diversas aminas, haluros de arilo y reactivos de alquilzinco.
  • Los conocimientos mecánicos sugieren un efecto de ligando cooperativo que involucra nitriles orgánicos y alquenos con deficiencia de electrones.