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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred to as...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Nickel/Photoredox Dual-Catalyzed Migratory Reductive C(sp2)-H/Si-Cl Cross-Coupling.

Kailin Yin1, Yuhang Wang1, Dongbing Zhao1

  • 1State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, China.

Angewandte Chemie (International Ed. in English)
|May 30, 2026
PubMed
Summary

This study introduces a novel nickel/photoredox dual-catalyzed method for remote C-H silylation using chlorosilanes. This breakthrough enables efficient synthesis of complex organosilicon compounds and silicon-containing polymers.

Keywords:
1,4‐nickel migrationC–Si bond formationchlorosilanesreductive coupling

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Area of Science:

  • Organosilicon Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Organosilicon compounds are vital in industry and academia.
  • Migratory cross-coupling enables remote C-H functionalization.
  • C-Si bond formation via migratory cross-coupling was previously unreported.

Purpose of the Study:

  • To develop a novel method for remote C-H silylation.
  • To achieve site-selective ipso/ortho-difunctionalization of aryl bromides.
  • To explore the synthesis of diverse arylsilanes and silicon-containing materials.

Main Methods:

  • Nickel/photoredox dual catalysis.
  • Visible-light irradiation.
  • Utilizing chlorosilanes for C-Si bond formation.

Main Results:

  • First formal remote C(sp2)-H silylation achieved.
  • Site-selective ipso/ortho-difunctionalization of aryl bromides.
  • Broad scope of multisubstituted arylsilanes synthesized with high selectivity.
  • Demonstrated utility in downstream transformations and polymer synthesis.

Conclusions:

  • The developed protocol offers a new pathway for organosilicon synthesis.
  • The method is efficient, selective, and avoids stoichiometric metallic reductants.
  • Highlights potential applications in complex molecule synthesis and materials chemistry.