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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 stereochemistry.
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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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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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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
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Hidroximetilación reductora catalizada por el cobre altamente regioselectiva y enantioselectiva de estirenos y

Yong-Yuan Gui1, Naifu Hu1, Xiao-Wang Chen1

  • 1Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, P. R. China.

Journal of the American Chemical Society
|November 11, 2017
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Resumen

Este estudio introduce una nueva reacción catalizada por el cobre utilizando dióxido de carbono (CO2) para crear alcoholes quirales a partir de estirenos y dienos. Este método eficiente produce alcoholes homobencílicos y homoalílicos valiosos, útiles en la síntesis de compuestos bioactivos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química ecológica

Sus antecedentes:

  • Los alcoholes quirales son bloques de construcción cruciales en los productos farmacéuticos y naturales.
  • El desarrollo de métodos eficientes y selectivos para la síntesis de alcoholes quirales sigue siendo un desafío importante en la síntesis orgánica.

Objetivo del estudio:

  • Desarrollar una hidroximetilación reductora catalizada por el cobre de estirenos y 1,3-dienos de alta regionalidad y enantioselectividad.
  • Para utilizar el dióxido de carbono (CO2) como fuente de C1 en condiciones suaves (1 atm).

Principales métodos:

  • Reacción de hidroximetilación reductora catalizada por el cobre.
  • Utilizando estirenos y 1,3-dienos como sustratos.
  • Utilizando 1 atm de dióxido de carbono (CO2) como reactivo.

Principales resultados:

  • Altos rendimientos de alcoholes homobencílicos quirales de los estirenos.
  • Excelentes selectividades regionales, enantiológicas y Z/E para los alcoholes quirales homoalílicos de 1,3-dienos.
  • Síntesis exitosa de compuestos bioactivos, incluido el curcumeno (R) y el ibuprofeno (S).
  • Los estudios mecanicistas indicaron la carboxilación de complejos de feniletilcobre con CO2 como un paso clave.

Conclusiones:

  • El método desarrollado proporciona una vía versátil y eficiente para obtener alcoholes quirales valiosos.
  • La utilidad de la reacción se demuestra por su amplio alcance de sustrato y fácil modificación del producto.
  • Este enfoque ofrece una alternativa más ecológica para sintetizar moléculas complejas utilizando CO2.