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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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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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Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

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Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
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Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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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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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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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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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

4.9K
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.
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Arrojar luz sobre las funciones ocultas del litio en el acoplamiento cruzado catalizado por níquel de éteres de arilo

Haosheng Liang1, Andryj M Borys2, Eva Hevia2

  • 1Université de Lyon, Université Claude Bernard Lyon I, CNRS, INSA, CPE, UMR 5246, ICBMS, Rue Victor Grignard, Villeurbanne Cedex F-69622, France.

Journal of the American Chemical Society
|August 30, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio revela cómo los intermediarios de níquel de litio permiten el acoplamiento cruzado de éter de arilo catalizado por níquel. Comprender estos mecanismos supera desafíos como el "problema del naftaleno", lo que permite una aplicación más amplia de este método sintético.

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Área de la Ciencia:

  • Química organometálica
  • Catálisis
  • Química orgánica sintética

Sus antecedentes:

  • El acoplamiento cruzado catalizado por níquel de éteres de arilo es vital para sintetizar aromáticos funcionalizados.
  • Los niquelados heterobimetálicos son intermediarios clave en estas reacciones, lo que permite condiciones suaves.
  • Estudios anteriores sugirieron su participación, pero los mecanismos detallados seguían sin estar claros.

Objetivo del estudio:

  • Investigar el mecanismo de acoplamiento cruzado catalizado por Ni ((COD) 2) de 2-metoxinaftaleno con PhLi.
  • Para aclarar la especiación y el papel de los intermediarios de níquel de litio.
  • Para explicar la influencia del disolvente y el litio en la reacción.

Principales métodos:

  • Cálculos de la Teoría Funcional de la Densidad (DFT).
  • Comparación con datos espectroscópicos y cinéticos experimentales.
  • Análisis de la especiación del nicelato de litio.

Principales resultados:

  • Conocimientos mecanicistas detallados sobre la reacción de acoplamiento cruzado catalizada por Ni.
  • Identificación de las especies clave de níquel de litio que apoyan el ciclo catalítico.
  • Explicación del papel crucial del disolvente y las múltiples funciones del litio.

Conclusiones:

  • El estudio proporciona una comprensión mecanicista completa del acoplamiento del éter de arilo catalizado por níquel.
  • Este conocimiento aborda el "problema del naftaleno", permitiendo el acoplamiento cruzado de diversos éteres de arilo.
  • Los hallazgos allanan el camino para aplicaciones más amplias de esta metodología sintética en condiciones suaves.