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Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Aminación C-H Alilica Intermolecular en Estadio Tardío

Takafumi Ide1, Kaibo Feng1, Charlie F Dixon1

  • 1Department of Chemistry, Roger Adams Laboratory, University of Illinois, 505 South Mathews Avenue, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|September 13, 2021
PubMed
Resumen

Este estudio introduce un catalizador de manganeso para la aminación alelica selectiva de fase tardía de moléculas complejas. Este avance permite la introducción eficiente de nitrógeno en los productos naturales, alterando potencialmente su actividad biológica.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis de productos naturales

Sus antecedentes:

  • La funcionalización C-H alilica es clave para la modificación de productos naturales.
  • La aminación alilica intermolecular se enfrenta a desafíos en la reactividad y la selectividad, lo que limita el alcance del sustrato.

Objetivo del estudio:

  • Desarrollar un método selectivo y eficiente para la aminación intermolecular de C-H.
  • Permitir la funcionalización en fase avanzada de moléculas orgánicas diversas y complejas, incluidos los productos naturales.

Principales métodos:

  • Se utilizó un catalizador de percloroftalocianina de manganeso sostenible ([MnIII(ClPc) ]).
  • Investigó la aminación de 32 compuestos cíclicos y lineales, incluidos aquellos con grupos funcionales competidores.
  • Se han realizado estudios mecanicistas para comprender la selectividad de los catalizadores.

Principales resultados:

  • Se ha logrado una aminación intermolecular selectiva y preparativa de C-H a través de una gama de sustratos.
  • Se ha demostrado una alta selectividad de sitio, región y diastereo (> 20: 1) en la funcionalización de productos naturales en etapa tardía.
  • La naturaleza electrofílica y voluminosa del catalizador, junto con un mecanismo escalonado, contribuyen a la selectividad.

Conclusiones:

  • El catalizador [MnIII(ClPc) ] ofrece una solución robusta para las reacciones de aminación alelica desafiantes.
  • Este método avanza significativamente las estrategias de funcionalización de última etapa para productos naturales y moléculas complejas.
  • La selectividad del catalizador amplía la aplicabilidad de la aminación alilica en la química sintética.