Video Experimental Relacionado

Updated: Mar 26, 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

La generación de radicales alcoxilo inducida por la luz visible permite la escisión y la funcionalización selectiva

Kunfang Jia¹, Fuyuan Zhang², Hanchu Huang¹

¹State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|February 2, 2016

Resumen

Este estudio introduce un nuevo método para generar radicales alcoxilo utilizando luz visible y catálisis de yodo, evitando condiciones adversas. Este avance permite la escisión selectiva de enlaces C-C y nuevas aplicaciones sintéticas con varios alcoholes.

Área de la Ciencia:

Química orgánica
Fotocatálisis
La Química Radical

Sus antecedentes:

Los radicales alkoxilo son intermediarios clave en la síntesis orgánica y en los estudios mecanicistas.
Los métodos actuales para la generación de radicales alcoxílicos requieren metales de transición y condiciones oxidativas severas.

Objetivo del estudio:

Desarrollar un método suave y eficiente para la generación de radicales alcoxilo.
Para explorar nuevas transformaciones sintéticas utilizando radicales alcoxilo.

Principales métodos:

Oxidación de los alcoholes inducida por la luz visible.
Catálisis con reactivos cíclicos de yodo.
Fragmentación β de los radicales alcoxilo.

Principales resultados:

Generación exitosa de radicales alcoxilo bajo condiciones de luz visible suave.
Se trata de la separación selectiva de los enlaces C(sp(3)) -C(sp(3)) en los cicloalcanoles con tensión.
Demostración de las reacciones de alquinilación y alquenilación con alcoholes tanto cíclicos como lineales.

Conclusiones:

La catálisis cíclica de yodo ofrece una vía nueva y leve para la generación de radicales alcoxilo.
Este método expande la utilidad sintética de los radicales alcoxilo en la química orgánica.

Más Videos Relacionados

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

Light-driven Enzymatic Decarboxylation

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Videos de Conceptos Relacionados

Radical Formation: Homolysis

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

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...

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.

Radical Reactivity: Nucleophilic Radicals

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...

Radical Formation: Addition

Radical Formation: Addition

Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...