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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Un enfoque diastereodivergente y enantioselectivo para las sin- y anti-diaminas: desarrollo de 2-azatrienos para

Pengfei Zhou1, Xinxin Shao2, Steven J Malcolmson1

  • 1Department of Chemistry, Duke University, Durham, North Carolina 27708, United States.

Journal of the American Chemical Society
|August 23, 2021
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Resumen
Este resumen es generado por máquina.

En este estudio se introducen los 2-azatrinos para la síntesis catalítica enantioselectiva de aminas alilicas. El acoplamiento reductor catalizado por cobre con iminas produce sin- o anti-1,2-diaminas, dependiendo del ligando utilizado.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis asimétrica

Sus antecedentes:

  • Las aminas alilicas son bloques de construcción cruciales en productos farmacéuticos y naturales.
  • El desarrollo de métodos catalíticos eficientes para la síntesis enantioselectiva de 1,2-diaminas sigue siendo un desafío importante en la química orgánica.

Objetivo del estudio:

  • Introducir los 2-azatrinos como una nueva clase de reactivos para la síntesis enantioselectiva catalítica.
  • Para demostrar la síntesis diastereodivergente de las sin- y las anti-1,2-diaminas utilizando 2-azatrinos.

Principales métodos:

  • El acoplamiento reductor catalizado por el cobre-bis (fosfina) de los 2-azatrinos con las iminas.
  • Utilizó Ph-BPE y t-Bu-BDPP como ligandos de apoyo para controlar la diastereoselectividad.

Principales resultados:

  • Se obtienen altos rendimientos y una excelente diastereoselectividad (> 20:1 dr) y enantioselectividad (> 99:1 er) para las anti-1,2-diaminas utilizando Ph-BPE.
  • Se obtienen sin-1,2-diaminas con alto rendimiento (hasta el 76%) y buena diastereoselectividad (1:> 20 dr) y enantioselectividad (97: 3 er) utilizando t-Bu-BDPP.

Conclusiones:

  • Los 2-azatrinos sirven como una plataforma versátil para la síntesis enantioselectiva catalítica de aminas alilicas.
  • El método desarrollado permite el acceso diastereodivergente tanto a las sin- como a las anti-1,2-diaminas simplemente cambiando el ligando de la fosfina.