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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.

Preparation of Alkynes: Alkylation Reaction

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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.

Ziegler–Natta Chain-Growth Polymerization: Overview

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...

Electrophilic Addition to Alkynes: Hydrohalogenation

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.

Formation of Halohydrin from Alkenes

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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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Updated: Jul 6, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

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Published on: January 17, 2020

Selective linear triene formation from different alkynes using Zr/Cu system.

Ken-ichiro Kanno¹, Eri Igarashi, Lishan Zhou

¹Catalysis Research Center and Graduate School of Life Science, Hokkaido University, and SORST, Japan Science and Technology Agency, Kita-ku, Sapporo 001-0021, Japan.

Journal of the American Chemical Society

|April 9, 2008

Summary

A novel one-pot method synthesizes linear trienes from three distinct alkynes using a zirconium/copper system. This efficient process offers a new route for creating complex organic molecules.

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Published on: June 21, 2017

Area of Science:

Organometallic Chemistry
Organic Synthesis
Catalysis

Background:

The synthesis of complex organic molecules like linear trienes is crucial in various chemical applications.
Existing methods for synthesizing linear trienes can be multi-step and lack efficiency.

Purpose of the Study:

To develop a selective and efficient one-pot procedure for synthesizing linear trienes from three different alkynes.
To explore the utility of a zirconium/copper catalytic system in this transformation.

Main Methods:

Preparation of a zirconacyclopentadiene intermediate from two distinct alkynes (alkyl-substituted and aryl-substituted).
Reaction of the zirconacyclopentadiene with N-chlorosuccinimide (NCS) to form a chlorodienylzirconocene intermediate.
Subsequent reaction with a third alkyne bearing electron-withdrawing groups in the presence of copper(I) chloride (CuCl) to yield the linear triene.

Main Results:

Successful selective synthesis of linear trienes in a single, one-pot procedure.
Demonstrated the formation of a key zirconacyclopentadiene intermediate.
Established the role of the Zr/Cu system in facilitating the coupling of three different alkynes.

Conclusions:

The developed Zr/Cu-catalyzed one-pot method provides an efficient route for the selective synthesis of linear trienes.
This methodology expands the synthetic toolbox for constructing complex polyalkyne structures.
The study highlights the potential of organozirconium intermediates in multi-component coupling reactions.