Video Experimental Relacionado

Updated: Apr 23, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Protección transitoria de las alquinas tensadas de la reacción de clic a través de la complejación con el cobre

Suguru Yoshida¹, Yasutomo Hatakeyama, Kohei Johmoto

¹Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.

Journal of the American Chemical Society

|September 19, 2014

Resumen

La protección transitoria de las cicloctinas mediante sales de cobre permite una química selectiva de clic. Este método permite la conjugación controlada en sitios específicos de alquina, lo que hace que los derivados de ciclooctina sean más accesibles para diversas aplicaciones.

Área de la Ciencia:

Química orgánica es la química orgánica.
Biología Química Biología química.

Sus antecedentes:

La química del clic, particularmente la cicloadición azida-alquina catalizada por cobre (CuAAC), es una herramienta poderosa para la construcción molecular.
Las cicloctinas son bloques de construcción versátiles, pero pueden sufrir reacciones no deseadas, lo que limita su utilidad.

Objetivo del estudio:

Desarrollar una estrategia de protección transitoria para las cicloctinas para prevenir reacciones prematuras.
Para permitir la funcionalización selectiva de las cicloctinas en presencia de otros grupos reactivos.

Principales métodos:

Complejación de ciclooctinas con una sal catiónica de cobre para formar un complejo 1:1, enmascarando temporalmente el alquino.
Aplicación del método de protección a las cicloctinas con fracciones terminales de alquino.
Conjugación selectiva de clic catalizada por cobre con azidas en el alquino terminal desprotegido.

Principales resultados:

La complejación del cobre impidió efectivamente que el cicloctino reaccionara con las azidas.
La conjugación selectiva se logró en el alquino terminal en presencia del alquino interno protegido.
Esta estrategia facilitó la síntesis de complejos derivados de la cicloctina.

Conclusiones:

Se ha establecido un nuevo método de protección transitoria para las cicloctinas utilizando sales de cobre.
Este método proporciona un control ortogonal en la química de clics, mejorando la accesibilidad de las ciclooctinas funcionalizadas.

Más Videos Relacionados

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

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 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.

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.

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.