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Regioselectivity and Stereochemistry of Hydroboration02:36

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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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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Introduction
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Borilación C3-Selectiva de Indolos sin Trazas y catalizada por Ni

Ya-Ming Tian1, Xiao-Ning Guo1, Zhu Wu1

  • 1Institut für Anorganische Chemie, and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

Journal of the American Chemical Society
|June 30, 2020
PubMed
Resumen
Este resumen es generado por máquina.

Un nuevo método catalizado por níquel permite la borilación C-H sin rastro y dirigida de los indolos en la posición C3. Este eficiente protocolo permite el posterior acoplamiento cruzado Suzuki-Miyaura, creando heteroarenas funcionales.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química Heterocíclica

Sus antecedentes:

  • La funcionalización C-H es una estrategia clave en la síntesis orgánica.
  • La funcionalización selectiva de los indoles sigue siendo un desafío.
  • La borilación dirigida de C-H ofrece una ruta versátil a los heteroarenos funcionalizados.

Objetivo del estudio:

  • Desarrollar un protocolo general y altamente eficiente para la borilación C3-selectiva y dirigida de los indolos.
  • Para utilizar un catalizador de níquel para esta transformación.
  • Para permitir la funcionalización posterior a través de reacciones de acoplamiento cruzado.

Principales métodos:

  • Utilizando un catalizador de níquel, específicamente [Ni(IMes) 2], para la berilación de C-H.
  • Utilizando la borilación del enlace N-H como una estrategia de grupo de dirección sin rastro.
  • Realización de reacciones con el bis ((pinacolato) diboro (B2pin2).

Principales resultados:

  • Se ha logrado una borilación C3 altamente eficiente y selectiva de varios indolos sustituidos.
  • Demostró la naturaleza sin rastro del grupo de dirección de la N-borilación, que se elimina in situ.
  • Se obtienen excelentes rendimientos para la reacción de borilación.
  • Se ha acoplado con éxito los indoles borilados C a través del acoplamiento cruzado Suzuki-Miyaura.

Conclusiones:

  • El protocolo desarrollado proporciona un método eficiente y operacionalmente simple para la síntesis de indol funcionalizado con C3.
  • Este enfoque ofrece una herramienta valiosa para la construcción de compuestos heterocíclicos complejos.
  • El proceso de una olla y dos pasos agiliza la síntesis de heteroarenos funcionalizados con C3.