Video Experimental Relacionado

Updated: May 9, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Síntesis de amida redox-neutral y de un solo paso catalizada por rutenio a partir de alcohol y nitrilo con economía

Byungjoon Kang¹, Zhenqian Fu, Soon Hyeok Hong

¹Center for Nanoparticle Research, Institute for Basic Science, Seoul 151-742, Republic of Korea.

Journal of the American Chemical Society

|August 7, 2013

Resumen

Este estudio presenta una nueva síntesis catalítica de amida utilizando alcoholes y nitriles. La reacción atómico-económica y redox-neutral forma enlaces de amida de manera eficiente sin subproductos, utilizando un catalizador de rutenio.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

La síntesis tradicional de amida a menudo requiere condiciones duras, múltiples pasos y genera desechos significativos.
El desarrollo de rutas sintéticas atómicamente económicas y neutras en redox es crucial para la química sostenible.
Los métodos catalíticos ofrecen vías eficientes para la construcción de moléculas complejas.

Objetivo del estudio:

Desarrollar una nueva síntesis de amida catalítica completamente atómica-económica y redox-neutral.
Para utilizar materiales de partida fácilmente disponibles: alcoholes y nitriles.
Para demostrar la utilidad del método desarrollado para sintetizar amidas etiquetadas con isótopos.

Principales métodos:

Empleó un catalizador de rutenio basado en carbenos N-heterocíclicos.
Facilitó el acoplamiento directo de un alcohol y un nitrilo.
Operado en condiciones de oxidación-reducción neutra, evitando oxidantes externos o reductores.

Principales resultados:

Se logró la formación eficiente de enlaces amida-C-N entre el nitrógeno nitrilo y el alcohol α-carbono.
La reacción procedió sin la generación de ningún subproducto, lo que demuestra una economía atómica completa.
Sintetizó con éxito amidas etiquetadas con isótopos (13) C o (15) N, mostrando la versatilidad del método.

Conclusiones:

Se ha establecido una síntesis de amida catalítica altamente eficiente, atómico-económica y redox-neutral a partir de alcoholes y nitriles.
La metodología desarrollada catalizada por rutenio ofrece una ruta sostenible y directa a las amidas.
La utilidad de la reacción se destaca aún más por su aplicación en la síntesis directa de compuestos de amida etiquetados.

Más Videos Relacionados

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphos^Ph Complexes

Published on: April 10, 2015

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Videos de Conceptos Relacionados

Preparation of Amines: Reduction of Amides and Nitriles

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,...

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Nitriles to Amines: LiAlH4 Reduction

Nitriles to Amines: LiAlH₄ Reduction

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...

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...