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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

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Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
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La macrolactonización a través de la oxidación de hidrocarburos.

Kenneth J Fraunhoffer1, Prabagaran Narayanasamy, Lauren E Sirois

  • 1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|July 13, 2006
PubMed
Resumen

Una nueva reacción catalizada por el paladio permite la macrolactonización de los ácidos omega-alcenoicos. Este método eficiente demuestra un amplio alcance de sustrato y una alta tolerancia de grupo funcional, útil para la síntesis de moléculas complejas.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La catálisis por catálisis.
  • Metodología sintética de la metodología sintética.

Sus antecedentes:

  • La macrolactonización es una transformación crucial en la síntesis de productos naturales complejos y productos farmacéuticos.
  • Los métodos existentes a menudo requieren condiciones duras o carecen de amplia compatibilidad de grupo funcional.

Objetivo del estudio:

  • Desarrollar una nueva reacción de macrolactonización catalizada por el paladio, eficiente y de amplia aplicación.
  • Para investigar el mecanismo de reacción y el alcance de la síntesis de diversas lactonas.

Principales métodos:

  • Utilizó un nuevo sistema catalítico Pd/sulfóxido para la macrolactonización de ácidos omega-alcenoicos lineales.
  • Empleó la vía de oxidación C-H alilica catalizada por ligando en serie.
  • Se investigó el alcance de la reacción con varios ácidos arilo, alquilo y insaturados, y se evaluó la compatibilidad del grupo funcional.

Principales resultados:

  • Se logró una macrolactonización eficiente de ácidos omega-alquenoicos a través de un nuevo sistema catalítico Pd/sulfóxido.
  • Amplio alcance de sustrato demostrado, incluidos los ácidos insaturados (Z) -alfa, beta sin isomerización.
  • Mostró una alta compatibilidad de grupo funcional con fracciones biológicamente relevantes como péptidos y ésteres.

Conclusiones:

  • La reacción reportada catalizada por Pd/sulfóxido proporciona una nueva y poderosa herramienta para la síntesis de macrolactona.
  • La reacción procede a través de la funcionalización de la esfera interna a partir de un intermediario carboxilato pi-allylPd carboxilado con plantilla.
  • Esta metodología ofrece ventajas significativas en términos de eficiencia, alcance y tolerancia del grupo funcional para la síntesis de moléculas complejas.