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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.

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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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.

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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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.

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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.

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Updated: Mar 22, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Published on: October 18, 2019

Highly Active Multidentate Ligand-Based Alkyne Metathesis Catalysts.

Ya Du¹, Haishen Yang¹, Chengpu Zhu¹

¹Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO, 80309, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|April 27, 2016

Summary

New molybdenum catalysts with tris(2-hydroxylbenzyl)methane ligands enable efficient alkyne metathesis. These stable and active catalysts demonstrate broad functional-group tolerance for challenging substrates.

Keywords:

alkylidyne alkyne metathesis homogeneous catalysis molybdenum multidentate ligand

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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

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Published on: August 23, 2018

Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Alkyne metathesis is a powerful synthetic tool.
Development of stable and active catalysts remains a challenge.
Molybdenum-based catalysts offer potential for alkyne transformations.

Purpose of the Study:

To develop novel molybdenum(VI) propylidyne catalysts for alkyne metathesis.
To investigate the stability, activity, and functional-group tolerance of these catalysts.
To explore the structure-activity relationship of the multidentate ligands.

Main Methods:

Synthesis of molybdenum(VI) propylidyne complexes with tris(2-hydroxylbenzyl)methane ligands.
Evaluation of catalytic performance in homodimerization and cyclooligomerization reactions.
Systematic investigation of ligand structure effects on catalyst stability and activity.

Main Results:

Developed highly stable (months at room temperature) and active molybdenum catalysts.
Achieved efficient homodimerization and cyclooligomerization of various alkyne substrates, including heterocycles.
Demonstrated broad functional-group tolerance under mild reaction conditions (40-55°C).

Conclusions:

The developed molybdenum catalysts exhibit exceptional stability and activity for alkyne metathesis.
The ortho groups on the tris(2-hydroxylbenzyl)methane ligand are crucial for catalyst performance.
These catalysts represent a significant advancement for synthetic applications involving alkynes.