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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.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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...

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic Aromatic Substitution: Addition–Elimination (S_NAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Alkyne migratory functionalization via C(sp³)-C(sp³) bond transposition.

Ming-Qiao Tang¹, Hao-Ran Xu², Xian-Xiao Chen¹

¹State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, China.

Nature Communications

|May 5, 2026

Summary

This study introduces migratory alkyne functionalization, a novel remote C-H activation strategy. It enables stereocontrolled hydroalkylation and hydroamination, offering a new pathway for chemical synthesis.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Published on: September 18, 2016

Area of Science:

Organic Chemistry
Catalysis
C-H Activation

Background:

Metal-walking strategies are established for remote C-H activation of alkenes.
Alkyne hydrofunctionalization typically involves in situ transformations, with remote protocols being underexplored.

Purpose of the Study:

To explore and demonstrate a novel migratory alkyne functionalization strategy.
To develop a remote protocol for alkyne hydroalkylation and hydroamination.
To investigate the potential for asymmetric activation of multiple C(sp3)-H bonds.

Main Methods:

Utilized three types of alkynes and two types of nucleophiles.
Employed mechanistic studies and computational calculations.
Performed gram-scale synthesis and downstream functionalization reactions.

Main Results:

Achieved migratory hydroalkylation and hydroamination of alkynes with good stereocontrol.
Demonstrated the concept's reliability and practical value through gram-scale tests.
Uncovered a 1,3-diene formation-driven allylic C(sp3)-C(sp3) bond transposition mechanism.

Conclusions:

Established a proof-of-concept for migratory alkyne functionalization, expanding remote C-H activation.
The developed method allows for stereoconvergent synthesis by transforming undesired regioisomers.
Highlights a potential new route for activating multiple inert C(sp3)-H bonds.