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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.

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

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.

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.

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.

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Updated: Jul 27, 2025

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

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

Published on: February 16, 2020

Hydroarylation of alkynes

Nilay Kumar Pal¹, Moumita Patra¹, Prabhakar K Pandey¹

¹Department of Chemistry and Centre for Environmental Sciences and Engineering Indian Institute of Technology Kanpur, Kanpur 208016, India. jbera@iitk.ac.in.

Chemical Communications (Cambridge, England)

|June 9, 2023

Summary

A novel dicopper complex catalyzes dual C-H functionalization of diaryl amines, enabling efficient synthesis of dihydroacridine derivatives via alkyne hydroarylation without directing groups.

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Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Direct C-H functionalization offers atom-economical synthetic routes.
Developing catalysts for sequential C-H activation remains a challenge.
Diaryl amines are versatile precursors for heterocyclic compounds.

Purpose of the Study:

To develop a novel catalyst for dual ortho-C-H functionalization.
To synthesize 9,10-dihydroacridine derivatives efficiently.
To explore the catalytic activity of a dicopper(I,I)-NHC complex.

Main Methods:

Synthesis of a pyridine and morpholine-functionalized dicopper(I,I)-NHC complex.
Catalytic testing of the complex in dual ortho-C-H functionalization reactions.
Hydroarylation of alkynes with diaryl amines.

Main Results:

The dicopper complex exhibits both terminal and bridging NHC coordination modes.
Catalyst 1 successfully mediates dual ortho-C-H activation of diaryl amines.
A wide range of 9,10-dihydroacridine derivatives were synthesized without directing groups.
The bimetallic construct enables sequential C-H bond activation.

Conclusions:

A pyridine and morpholine-functionalized dicopper(I,I)-NHC complex is an effective catalyst for dual ortho-C-H functionalization.
This methodology provides a direct route to diverse 9,10-dihydroacridine derivatives.
The catalyst's ability to activate sequential C-H bonds offers synthetic advantages.