Video Experimental Relacionado

Updated: Jun 7, 2025

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

Oxidación catalizada por oxamonio de aminas sustituidas

Jonas Rein¹, Bartosz Górski¹, Yukun Cheng¹

¹Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.

Journal of the American Chemical Society

|November 11, 2024

Resumen

Los investigadores desarrollaron un nuevo método de oxidación catalizado por oxoamonio para las aminas sustituidas por N. Esta eficiente reacción de transferencia de hidruro convierte varios derivados de aminas en imidas, con una aplicación exitosa a gran escala en sistemas de flujo continuo.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las reacciones de oxidación son fundamentales en la síntesis orgánica.
El desarrollo de sistemas catalíticos eficientes para la funcionalización de aminas sigue siendo un desafío clave.

Objetivo del estudio:

Desarrollar una nueva oxidación catalizada por oxoamonio de aminas sustituidas por N.
Para lograr la síntesis de imidas a partir de una amplia gama de derivados de aminas.

Principales métodos:

Utilizados catalizadores de oxoamonio con propiedades estéricas y electrónicas adaptadas.
Se utiliza un mecanismo de transferencia de hidrógeno para el proceso de oxidación.
Se han investigado condiciones de reacción complementarias para diversos sustratos.

Principales resultados:

Oxida con éxito carbamatos, sulfonamidas, ureas y amidas a sus correspondientes imidas.
Demostró el amplio alcance y la aplicabilidad del método desarrollado.
Validación de la reacción en una escala de 100 g utilizando tecnología de flujo continuo.

Conclusiones:

La oxidación catalizada por oxoammonio desarrollada proporciona una ruta eficiente a las imidas.
El método ofrece un enfoque versátil y escalable para la funcionalización de aminas.
El procesamiento de flujo continuo permite la síntesis práctica a gran escala.

Más Videos Relacionados

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Videos de Conceptos Relacionados

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

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...

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,...

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

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...

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 Amines: Alkylation of Ammonia and Amines

Preparation of Amines: Alkylation of Ammonia and Amines

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...

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...