Video Experimental Relacionado

Updated: Mar 1, 2026

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

C-alquilación catalizada por níquel de nitroalcanos con yoduros de alquilo no activados

Sina Rezazadeh¹, Vijayarajan Devannah¹, Donald A Watson¹

¹Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.

Journal of the American Chemical Society

|June 9, 2017

Resumen

Un nuevo método catalizado por níquel permite una ligera alquilación C de los nitroalcanos utilizando yoduros de alquilo simples. Esta reacción versátil es compatible con varios grupos alquilo y grupos funcionales, ofreciendo una síntesis eficiente de diversos nitroalcanos.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los nitroalcanos son productos intermedios sintéticos muy versátiles.
La C-alquilación de los nitroalcanos es una transformación clave.
Los métodos existentes a menudo requieren condiciones duras o sustratos específicos.

Objetivo del estudio:

Desarrollar un método catalítico suave y general para la C-alquilación de los nitroalcanos.
Utilización de ioduros de alquilo no activados como agentes alquilantes.
Ampliar el alcance de la funcionalidad de los nitroalcanos.

Principales métodos:

La reacción catalizada por el níquel.
Uso de ioduros de alquilo primarios, secundarios y terciarios.
Condiciones de reacción leves.

Principales resultados:

C-alquilación exitosa de los nitroalcanos con yoduros de alquilo no activados.
Alta tolerancia al grupo funcional, incluidos los ioduros alquilo primarios, secundarios y terciarios.
Acceso rápido a una amplia gama de nitroalcanos funcionales.

Conclusiones:

Se ha establecido un método suave, general y eficiente catalizado por níquel para la C-alquilación de nitroalcanos.
Este método proporciona una herramienta valiosa para sintetizar derivados complejos de nitroalcanos.
El amplio alcance de la reacción y la tolerancia del grupo funcional lo hacen altamente aplicable en la síntesis orgánica.

Más Videos Relacionados

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Videos de Conceptos Relacionados

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

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...

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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,...