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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
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Catálisis EnT habilitada, ciclación en cascada de relevo radicalario para acceder a ciclohexano/ciclohexeno

Mei Xiang1, Cong Huang1, Jie Gao1

  • 1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China. hyangchem@csu.edu.cn.

Chemical communications (Cambridge, England)
|December 24, 2025
PubMed
Resumen

La catálisis de transferencia de energía triplete-triplete (EnT) mediada por luz visible permite la síntesis eficiente de marcos de ciclohexano y ciclohexeno multissustituidos. Esta novedosa estrategia de ciclación de relevo radicalario utiliza un reactivo bifuncional para un amplio alcance de sustratos y alta diastereoselectividad.

Palabras clave:
catálisisquímica orgánicafotocatálisisrelevo radicalariociclacióntransferencia de energía triplete-tripletequímica sostenible

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Área de la Ciencia:

  • Química Orgánica
  • Catálisis
  • Fotoquímica

Sus antecedentes:

  • La fotocatálisis con luz visible es un campo en rápida expansión.
  • La catálisis de transferencia de energía triplete-triplete (EnT) ofrece vías de reactividad únicas.
  • El desarrollo de métodos eficientes para sintetizar marcos cíclicos complejos es crucial.

Objetivo del estudio:

  • Desarrollar una novedosa estrategia de ciclación de relevo radicalario catalizada por EnT.
  • Sintetizar diversos marcos de ciclohexano y ciclohexeno multissustituidos.
  • Explorar la utilidad de un reactivo bifuncional diseñado racionalmente.

Principales métodos:

  • Irradiación con luz visible.
  • Catálisis de transferencia de energía triplete-triplete (EnT).
  • Ciclación de relevo radicalario.
  • Se utilizó un novedoso reactivo bifuncional: óxido de difenilmetano O-(2,2-dimetil-4-fenilpent-4-enilo).

Principales resultados:

  • Síntesis exitosa de varios marcos de ciclohexano y ciclohexeno multissustituidos.
  • Demostró un amplio alcance de sustratos con alquenos y alquinos.
  • Logró una excelente diastereoselectividad en las reacciones de ciclación.
  • Mostró la fácil conversión de los productos de ciclohexano en derivados de 6-azabiciclo[3.2.1]octan-7-ona.

Conclusiones:

  • La ciclación de relevo radicalario catalizada por EnT desarrollada es un método conciso y eficaz.
  • El reactivo bifuncional sirve como precursores de radicales duales para transformaciones eficientes.
  • Este enfoque proporciona una ruta respetuosa con el medio ambiente hacia moléculas cíclicas complejas.