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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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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Activación de enlaces C-H controlada por la basicidad por un complejo Ni (III) -hidroxo estructuralmente

Hung-Ruei Pan1, John Wu1, Chun-Ming Tsai1

  • 1Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.

Journal of the American Chemical Society
|July 25, 2025
PubMed
Resumen

Los investigadores desarrollaron un complejo de níquel-hidroxo estable que activa fuertes enlaces C-H. Este descubrimiento ofrece nuevos conocimientos sobre los mecanismos de la oxidación selectiva y las reacciones de transferencia de átomos de hidrógeno.

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Área de la Ciencia:

  • Química organometálica
  • Catálisis
  • Química sintética

Sus antecedentes:

  • La oxidación selectiva de enlaces fuertes C-H es un desafío significativo en la química sintética.
  • Los mecanismos y los oxidantes activos para la activación del enlace C-H no se comprenden completamente.
  • El desarrollo de complejos meta-oxo o meta-hidroxo estables y reactivos es crucial.

Objetivo del estudio:

  • Aislar y caracterizar un nuevo complejo mononuclear de Ni (III) -hidroxo.
  • Investigar las capacidades de activación de enlaces C-H del complejo Ni (III) -hidroxo.
  • Para aclarar el mecanismo de la transferencia de átomos de hidrógeno (HAT) y la transferencia de electrones acoplados a protones (PCET).

Principales métodos:

  • Aislamiento y caracterización completa del complejo Ni (III) -hidroxo mediante cristalografía de rayos X.
  • Estudios de reactividad de transferencia de átomos de hidrógeno (HAT) con varios sustratos C-H, incluido el ciclohexano.
  • Estudios cinéticos para correlacionar las velocidades de reacción con las propiedades del sustrato (pKa, BDE).
  • Análisis semiempírico de la energía libre para determinar el grado de transferencia de protones (PT).

Principales resultados:

  • Se sintetizó y caracterizó con éxito un complejo mononuclear Ni (III) -hidroxo estable a temperatura ambiente, [Na (c5) ] [Ni (PS3) ].
  • El complejo 2 demostró la reactividad de transferencia de átomos de hidrógeno (HAT) hacia enlaces C-H fuertes.
  • Los estudios cinéticos indicaron una vía PCET asincrónica, predominantemente regida por la transferencia de protones (PT), con un valor de mejor ajuste x de 0,18.
  • Se determinó que la energía libre de disociación del enlace O-H de las especies de Ni (II) -agua resultantes era de 96,6-100,3 kcal mol-1.

Conclusiones:

  • El complejo Ni (III) -hidroxo 2 es un oxidante raro y bien definido capaz de activar fuertes enlaces C-H.
  • La basicidad del sustrato juega un papel crítico en la modulación de la reactividad del PCET.
  • Los hallazgos proporcionan información mecanicista valiosa sobre la oxidación de enlaces C-H mediada por especies de metal-hidroxo.