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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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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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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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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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.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Cambio en selectividades por catálisis dinuclear de níquel: hidroarilación de 1,3-dienes a Z-olefinas

Ke Chen1,2, Hongdan Zhu3, Shuang Liu2

  • 1Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.

Journal of the American Chemical Society
|October 30, 2023
PubMed
Resumen

Los investigadores desarrollaron un catalizador de dinickel que cambia la selectividad de hidroarilación común. Este nuevo enfoque permite la síntesis de Z-olefinas desafiantes, isómeros previamente inaccesibles, a través de la 1,4-hidroarilación.

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Área de la Ciencia:

  • Síntesis orgánica
  • Catálisis
  • Química organometálica

Sus antecedentes:

  • El control de la selectividad en la síntesis orgánica es un desafío importante, especialmente para acceder a isómeros anteriormente inaccesibles.
  • Los complejos metálicos binucleares ofrecen un potencial de reactividad y selectividad únicos en comparación con los catalizadores mononucleares, inspirados en sistemas biológicos.

Objetivo del estudio:

  • Investigar el uso de un complejo macrocíclico de bispiridil diimine dinickel para la hidroarilación de 1,3-dienos.
  • Cambiar la selectividad de 4,3-región establecida por una vía alternativa de 1,4-hidroariación.
  • Para lograr una Z-estereoselectividad termodinámicamente menos estable, dando lugar a objetivos difíciles de Z-olefina.

Principales métodos:

  • Catalización mediante el uso de un complejo macrocíclico de bispiridil dimina diníquel.
  • Hidroarilación de los 1,3-dienos.
  • Cálculos de la Teoría Funcional de la Densidad (DFT) para elucidar los mecanismos de reacción.

Principales resultados:

  • El catalizador de dinickel cambió con éxito la regioselectividad de 4,3- a 1,4-hidroarilación.
  • La reacción produjo Z-olefinas con Z-estereoselectividad, un resultado termodinámicamente menos favorecido.
  • Los cálculos de DFT revelaron que la coordinación dinuclear del Ni-diolefin y los efectos sinérgicos son cruciales para la reactividad y la selectividad observadas.

Conclusiones:

  • La catálisis de níquel binuclear, facilitada por un complejo de bispiridil diimina macrocíclico, permite un control sin precedentes sobre la selectividad de la hidroarilación.
  • Esta metodología proporciona acceso a las Z-olefinas de valor sintético.
  • Los efectos sinérgicos de los centros dinucleares son clave para lograr selectividades distintas de los catalizadores de níquel mononucleares.