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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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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...
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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.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Funcionalización alifática regioselectiva de C-H utilizando pares de radicales frustrados

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Resumen

Los pares de radicales frustrados (FRP) permiten la funcionalización del enlace C-H mediante la escisión de enlaces no activados. La adaptación de las estructuras de donantes permite el control de la reactividad hacia diferentes enlaces C-H, ofreciendo nuevas posibilidades sintéticas.

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Área de la Ciencia:

  • Química organometálica
  • La Química Radical
  • Síntesis orgánica

Sus antecedentes:

  • Los pares de Lewis frustrados (FLP) activan moléculas pequeñas a través de vías heterolíticas.
  • Las investigaciones emergentes muestran que los FLPs pueden formar pares de radicales a través de la transferencia de un solo electrón.
  • Los pares de radicales frustrados (FRP) son radicales estables con aplicaciones sintéticas limitadas.

Objetivo del estudio:

  • Demostrar la funcionalidad de los enlaces C(sp3)-H utilizando una nueva clase de FRP.
  • Explorar el potencial de los FRP como reactivos en la síntesis química.
  • Investigar la capacidad de ajuste de la reactividad y la regioselectividad del FRP.

Principales métodos:

  • Generación de FRP a partir de donantes de disilazida y aceptores de N-oxoamonio.
  • Aplicación de FRP para la escisión de enlaces C-H no activados.
  • Estudios mecanicistas para aclarar el papel de los pares de radicales en la reacción.

Principales resultados:

  • Funcionalización exitosa de los enlaces C ((sp3) -H que producen productos aminoxilados.
  • Demostración de la regioselectividad controlada mediante la modificación de las estructuras de los donantes.
  • Evidencia que apoya la formación y la participación de pares de radicales transitorios y persistentes.

Conclusiones:

  • Las FRP generadas a partir de donantes de disilazida y aceptores de N-oxoamonio son efectivas para la funcionalización del enlace C-H.
  • La reactividad de los FRP puede ajustarse a los enlaces C-H primarios, secundarios o terciarios.
  • Este trabajo expande la utilidad sintética de los pares de radicales frustrados.