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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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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.
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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

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The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the...
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Radical Formation: Addition00:47

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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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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

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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...
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Etapa tardía C2 - C3 Diversificación a través de complejos de adición oxidativa de níquel

Carlota Odena1,2, Tomás G Santiago1, María Lourdes Linares3

  • 1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Avenida Països Catalans 16, 43007 Tarragona, Spain.

Journal of the American Chemical Society
|July 25, 2024
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Resumen

Los complejos de adición oxidativa del níquel (Ni-OAC) ofrecen una nueva plataforma para el descubrimiento de fármacos. Este enfoque genera rápidamente candidatos a plomo con una fracción mejorada de C ((sp3)), acelerando el ciclo de diseño-fabricación-prueba-análisis.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Catálisis

Sus antecedentes:

  • El descubrimiento de fármacos a menudo se enfrenta a desafíos para acceder al nuevo espacio químico, particularmente con altas fracciones de C ((sp3).
  • Las reacciones catalizadas por níquel tradicionales pueden tener un alcance limitado y requieren ligandos especializados.

Objetivo del estudio:

  • Introducir complejos de adición oxidativa de níquel (Ni-OAC) como una plataforma versátil para la generación rápida de candidatos al plomo.
  • Explorar el potencial de los Ni-OAC para acceder a un nuevo espacio químico más allá de los acoplamientos C(sp2)-C(sp3).
  • Para demostrar un proceso automatizado de diversificación para acelerar el descubrimiento de fármacos.

Principales métodos:

  • Síntesis y caracterización de Ni-OACs derivados de moléculas similares a las drogas.
  • Evaluación de los Ni-OAC en varias reacciones de formación de enlaces, incluidos los acoplamientos C(sp2)-C(sp3).
  • Desarrollo e implementación de un flujo de trabajo automatizado de diversificación.

Principales resultados:

  • Los Ni-OAC permiten la generación rápida de candidatos al plomo con una fracción C ((sp3) mejorada.
  • Los Ni-OAC demuestran una amplia aplicabilidad en diversas formaciones de enlaces, superando los métodos convencionales catalizados por Ni.
  • El proceso automatizado de diversificación pone de relieve la solidez y la eficiencia de la plataforma Ni-OAC.

Conclusiones:

  • Los Ni-OAC proporcionan una estrategia poderosa y generalizable para acceder a nuevas entidades químicas.
  • Esta plataforma acelera significativamente el ciclo de diseño, fabricación, prueba y análisis (DMTA) en el descubrimiento de fármacos.
  • Los Ni-OAC representan una nueva puerta de entrada prometedora para la química medicinal y la optimización del plomo.