Video Experimental Relacionado

Updated: Jun 12, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Acoplamiento de tres componentes catalizado por oro: oxirilación oxidativa de alquenos

Asa D Melhado¹, William E Brenzovich, Aaron D Lackner

¹Department of Chemistry, University of California, Berkeley, California 94720, USA.

Journal of the American Chemical Society

|June 19, 2010

Resumen

Una nueva reacción catalizada por oro (I) acopla eficientemente a los alquenos, ácidos arilborónicos y nucleófilos de oxígeno. Este método proporciona una ruta versátil a los éteres, ésteres y alcoholes beta-arilo.

Área de la Ciencia:

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

Sus antecedentes:

El desarrollo de rutas sintéticas eficientes para moléculas orgánicas funcionalizadas es crucial en química.
La catálisis del oro ha surgido como una poderosa herramienta para diversas transformaciones orgánicas.
La funcionalización selectiva de alquenos sigue siendo un desafío sintético importante.

Objetivo del estudio:

Desarrollar una nueva reacción de acoplamiento de tres componentes.
Para utilizar alquenos terminales, ácidos arilborónicos y nucleófilos de oxígeno.
Para establecer una síntesis eficiente de compuestos oxigenados sustituidos por beta-arilo.

Principales métodos:

Empleando un complejo de bromuro de oro binuclear como el catalizador.
Utilizando Selectfluor como el oxidante estequiométrico.
Explorar el alcance de los nucleófilos de oxígeno, incluidos los alcoholes, los ácidos carboxílicos y el agua.

Principales resultados:

Acoplamiento exitoso de tres componentes de alquenos terminales, ácidos arilborónicos y nucleófilos de oxígeno.
Demostración de la eficiencia y versatilidad de la reacción.
Síntesis de éteres beta-arilo, ésteres y alcoholes a partir de materiales de partida simples.

Conclusiones:

La reacción catalizada por oro desarrollada ofrece un método eficiente y práctico para sintetizar compuestos oxigenados beta-arilo.
Esta metodología amplía la utilidad sintética de alquenos terminales y ácidos arilborónicos.
La reacción proporciona una nueva herramienta valiosa para la síntesis orgánica.

Más Videos Relacionados

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

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Videos de Conceptos Relacionados

Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...