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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.3K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.4K
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.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.4K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Acoplamiento electrocatalítico C-N a través de intermediarios de yodo hipervalentes generados anodicamente

Asim Maity1, Brandon L Frey1, Nathanael D Hoskinson1

  • 1Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.

Journal of the American Chemical Society
|March 5, 2020
PubMed
Resumen

Este estudio introduce la electrocatálisis de yodo hipervalente libre de metales para una síntesis orgánica eficiente y sostenible. La generación anódica de intermediarios de yodo hipervalentes permite nuevas reacciones de acoplamiento C-H y N-H, avanzando la electroquímica sintética.

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Área de la Ciencia:

  • Química orgánica
  • La electroquímica
  • Síntesis sostenible

Sus antecedentes:

  • La química electrosintética ofrece rutas sostenibles para la síntesis orgánica.
  • Los compuestos de yodo hipervalentes son reactivos versátiles en las transformaciones orgánicas.

Objetivo del estudio:

  • Desarrollar un sistema de electrocatálisis de yodo hipervalente libre de metales.
  • Para permitir reacciones eficientes de acoplamiento C-H/N-H utilizando la electroquímica.
  • Proporcionar conocimientos mecanicistas sobre la electroquímica mediada por yodo hipervalente.

Principales métodos:

  • Oxidación anódica de yoduros de arilo para generar intermedios de yodo hipervalentes.
  • Utilizando iones de acetato para la estabilización de los intermedios transitorios.
  • Aplicación del sistema desarrollado a las reacciones de formación de enlaces C-N intra e intermoleculares.

Principales resultados:

  • Acoplamiento eficaz demostrado de la transferencia interfacial de electrones con acoplamiento oxidativo C-H/N-H.
  • Se ha demostrado su aplicabilidad tanto en la formación de enlaces C-N intramoleculares como intermoleculares.
  • Se ha identificado un intermediario transitorio I(II) estabilizado por iones acetato.

Conclusiones:

  • Este trabajo presenta la primera electrocatálisis de yodo hipervalente libre de metales para la funcionalización C-H.
  • Los hallazgos ofrecen una comprensión mecanicista para el desarrollo futuro de mediadores de yodo hipervalentes en electroquímica sintética.
  • Este enfoque mejora la eficiencia y la sostenibilidad de la síntesis orgánica.