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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Preparation of Epoxides03:00

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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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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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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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.
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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Epoxidación selectiva de olefinas impulsada electroquímicamente por el catalizador de cobalto-TAML

Suyeon S Kim1, Sugyeong Hong2, Adarsh Koovakattil Surendran3

  • 1Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, South Korea.

Journal of the American Chemical Society
|January 29, 2025
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Resumen

Este estudio introduce una nueva epoxidación electrocatalítica utilizando un ligando macrocíclico de cobalto-tetramido (TAML). Este método sostenible convierte eficientemente las olefinas en epoxidas en condiciones ambientales utilizando el agua como fuente de oxígeno.

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Área de la Ciencia:

  • Química ecológica
  • Catálisis
  • La electroquímica

Sus antecedentes:

  • La conversión termoquímica de los epóxidos se enfrenta a desafíos que incluyen condiciones adversas y emisiones de gases de efecto invernadero.
  • Los epóxidos son productos intermedios cruciales en la fabricación de diversos productos industriales.
  • Es esencial desarrollar alternativas sostenibles para la síntesis de epóxidos.

Objetivo del estudio:

  • Desarrollar un método electrocatalítico alternativo y sostenible para la epoxidación de olefinas.
  • Para utilizar un catalizador molecular, para una epoxidación eficiente y selectiva.
  • Investigar el mecanismo de reacción e identificar los intermediarios activos.

Principales métodos:

  • Epoxidación electrocatalítica mediante el catalizador [CoIII (TAML) ]-.
  • Utilizando agua como fuente de átomos de oxígeno en condiciones ambientales.
  • Empleando estudios electrokinéticos, espectrometría de masas de ionización por electrospray (VESI-MS) y resonancia paramagnética de electrones (EPR) para conocimientos mecanicistas.

Principales resultados:

  • El catalizador [CoIII TAML]- demostró una alta selectividad (> 90%) y una eficiencia Faradaic (> 60%) para la epoxidación del ciclohexeno.
  • El catalizador exhibió un amplio alcance de sustrato para la epoxidación de olefinas.
  • Se identificó un proceso de transferencia de electrones acoplado a protones como el paso que limita la velocidad, formando especies reactivas de cobalto-oxígeno.

Conclusiones:

  • El catalizador Co-III ofrece una alternativa eficiente y sostenible a la epoxidación termoquímica tradicional.
  • Este enfoque electrocatalítico proporciona una nueva vía para la producción de valiosas materias primas químicas.
  • Los hallazgos allanan el camino para una síntesis química más ecológica utilizando métodos electroquímicos.