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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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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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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Co-Mabiq vuela solo: Markovnikov impulsado por la luz - Alquilación selectiva de C e N de los indoles e indazoles sin

Oaikhena Zekeri Esezobor1, Wenyi Zeng1, Lukas Niederegger1

  • 1Technical University of Munich, Department of Chemistry and Catalysis Research Center, Lichtenbergstr. 4, 85748 Garching, Germany.

Journal of the American Chemical Society
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Resumen

Este estudio introduce un nuevo método basado en la luz visible para la alquilación de indoles e indazoles utilizando catalizadores de cobalto. Este proceso eficiente logra altos rendimientos y regioselectividad para compuestos farmacéuticos valiosos.

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Área de la Ciencia:

  • Química orgánica
  • La fotoquímica
  • Catálisis

Sus antecedentes:

  • Los indolos y los indazoles son andamios cruciales en los productos farmacéuticos y naturales.
  • Es muy deseable desarrollar métodos eficientes de funcionalización para estos heterociclos.
  • La catálisis impulsada por la luz utilizando metales abundantes en la tierra ofrece un enfoque sostenible.

Objetivo del estudio:

  • Desarrollar un método inducido por luz visible para la alquilación C3 y N de los indolos e indazoles.
  • Para investigar la actividad catalítica de los complejos de cobalto con el ligando Mabiq.
  • Explorar el doble papel del complejo de cobalto como fotosensibilizador y catalizador.

Principales métodos:

  • Irradiación con luz visible de los indoles/indazoles con estirenos.
  • Catalización mediante el uso de complejos de cobalto, específicamente Co ((Mabiq) Cl2 y Co ((MabiqBr) Cl2.
  • Examen del comportamiento fotoquímico y la reactividad de los catalizadores de cobalto.

Principales resultados:

  • Exitosa C3- y N-alquilación de indolos e indazoles con estirenos.
  • Se alcanzaron altos rendimientos (hasta el 96%) y la selectividad regional de Markovnikov.
  • Demostró el doble papel del complejo de cobalto como fotosensibilizador y centro metálico activo.
  • El ligando de Mabiq proporciona el regiocontrol en las reacciones de alquilación.

Conclusiones:

  • Se ha desarrollado una alquilación novedosa, eficiente y regioselectiva de indolos e indazoles impulsada por luz visible.
  • Los complejos de cobalto-Mabiq son catalizadores efectivos para esta transformación, actuando tanto como fotosensibilizadores como como centros metálicos activos.
  • Este método proporciona una herramienta valiosa para sintetizar indolos e indazoles funcionalizados para aplicaciones farmacéuticas.