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Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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Aryne Generation from Aryl Halides Via Photothermal Red-Light Activation.

Cristina Preston-Herrera¹, Rory C Devin¹, Megan E Matter¹

¹Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|December 9, 2025

Summary

This summary is machine-generated.

This study introduces a new method for generating arynes using red light and photothermal conversion of aryl halides. This approach simplifies C-N bond formation for pharmaceuticals and agrochemicals without harsh conditions.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Area of Science:

Organic Chemistry
Synthetic Methodology
Photochemistry

Background:

Traditional aryne generation methods often require harsh conditions and lack atom economy.
Existing methods for mild aryne generation typically rely on activated precursors.
The Kobayashi method is a long-standing standard for aryne generation.

Purpose of the Study:

To develop a simplified method for generating arynes from readily available aryl or heteroaryl halides.
To enable mild aryne generation under ambient conditions using photothermal conversion.
To facilitate the synthesis of C-N bonds, crucial for pharmaceuticals and agrochemicals.

Main Methods:

Photothermal conversion of aryl or heteroaryl halides using red light irradiation.
Utilizing carbon black as a photothermal agent to create inhomogeneous thermal gradients.
Trapping of the generated aryne intermediate with nitrogen nucleophiles.

Main Results:

Successful generation of arynes from various aryl and heteroaryl halides in under 20 minutes.
Demonstrated C-N bond formation via amination, with regioselectivity supporting an aryne mechanism.
Showcased aryne trapping via [4 + 2] cycloaddition and with sulfur nucleophiles, alongside a double amination.

Conclusions:

The photothermal method provides on-demand access to arynes from simple aryl halides without inert conditions or additional synthetic steps.
This approach overcomes operational barriers associated with traditional aryne generation.
The developed method offers a simplified and efficient route to C-N bond formation for synthesizing valuable organic molecules.