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Related Concept Videos

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...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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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.
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

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Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...

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Electrophotocatalysis Enables Birch-Type Dearomative Alkylation.

Cheng Wang1,2, Ya-Jing Chen1,2, Wen-Jie Kang1,2

  • 1Key Laboratory of Supramolecular Photochemistry & CAS-HKU Joint Laboratory On New Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, P. R. China.

Angewandte Chemie (International Ed. in English)
|May 14, 2026
PubMed
Summary

This study introduces the first electrophotocatalytic Birch-type dearomative alkylation, enabling efficient synthesis of sp3-hybridized carbon centers in arenes. The novel method overcomes previous limitations, offering a direct route for modifying aromatic compounds.

Keywords:
birch‐type dearomatizationelectrophotocatalysistandem alkylation

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • Birch-type dearomative alkylation is key for creating sp3-hybridized carbon centers in (hetero)arenes.
  • Traditional methods face challenges like competitive protonation and poor alkylation control, yielding undesired 1,4-cyclohexadienes.

Purpose of the Study:

  • To develop the first electrophotocatalytic method for Birch-type dearomative alkylation of (hetero)arenes.
  • To enable efficient and selective alkylation of aromatic systems under mild conditions.

Main Methods:

  • Utilized N,N-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-bis(dicarboximide) as a metal-free electrophotocatalyst.
  • Employed alkyl chlorides as alkylating agents in a tandem reaction.
  • Investigated reaction mechanisms using control experiments, spectroscopic studies, and DFT calculations.

Main Results:

  • Successfully achieved dearomative alkylation of anthracene, naphthalene, and acridine derivatives.
  • Identified two reaction pathways: "Birch-SN2" and "XAT-SRN1" for arene radical anions reacting with alkyl chlorides.
  • Demonstrated high site selectivity and broad functional group tolerance.

Conclusions:

  • The developed electrophotocatalytic method provides a powerful new tool for the direct modification of (hetero)arenes.
  • The reaction proceeds under extremely mild conditions, utilizing simulated sunlight and solar electricity.
  • This approach shows significant potential for synthesizing complex aromatic frameworks.