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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.

Nomenclature of Alkynes

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

Nomenclature of Aryl and Heterocyclic Amines

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

Turnover Number and Catalytic Efficiency

Turnover Number and Catalytic Efficiency

The turnover number of an enzyme is the maximum number of substrate molecules it can transform per unit time. Turnover numbers for most enzymes range from 1 to 1000 molecules per second. Catalase has the known highest turnover number, capable of converting up to 2.8×106 molecules of hydrogen peroxide into water and oxygen per second. Lysozyme has the lowest known turnover number of half a molecule per second.
Chymotrypsin is a pancreatic enzyme that breaks down proteins during digestion....

Catalytically Perfect Enzymes

Catalytically Perfect Enzymes

The theory of catalytically perfect enzymes was first proposed by W.J. Albery and J. R. Knowles in 1976. These enzymes catalyze biochemical reactions at high-speed. Their catalytic efficiency values range from 108-109 M-1s-1. These enzymes are also called 'diffusion-controlled' as the only rate-limiting step in the catalysis is that of the substrate diffusion into the active site. Examples include triose phosphate isomerase, fumarase, and superoxide dismutase.

Most enzymes...

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

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Updated: Feb 7, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Catalytic Alkyne Arylation Using Traceless Directing Groups.

Jung-Woo Park^1,2, Bubwoong Kang¹, Vy M Dong¹

¹Department of Chemistry, University of California, Irvine, 4403 Natural Sciences 1, Irvine, California, 92697, USA.

Angewandte Chemie (International Ed. in English)

|August 2, 2018

Summary

This summary is machine-generated.

This study introduces a novel palladium-catalyzed three-component reaction for aminoarylation of alkynes, forming enamines. These intermediates can be converted into valuable ketones, showcasing a new C-C bond formation strategy using amines as directing groups.

Keywords:

alkynes aminoarylation multicomponent coupling palladium regiocontrol

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Traditional C-C bond formation methods often require harsh conditions or specific directing groups.
Developing efficient catalytic systems for complex molecule synthesis is a key challenge in organic chemistry.

Purpose of the Study:

To develop a novel palladium-catalyzed three-component reaction for the synthesis of enamines.
To explore the utility of enamines generated in situ for the synthesis of α-arylphenones and α,α-diarylketones.

Main Methods:

Utilized a palladium(0) catalyst supported by Mandyphos ligand.
Performed a three-component reaction involving alkynes and amines.
Hydrolyzed the resulting enamines to access ketone products.

Main Results:

Successfully synthesized enamines via a three-component aminoarylation of alkynes.
Demonstrated the hydrolysis of enamines to α-arylphenones and α,α-diarylketones.
Established a novel palladium-catalyzed pathway for C-C bond formation.

Conclusions:

The developed Pd-catalyzed method offers an efficient route to enamines and subsequent ketones.
This methodology enables the use of amines as traceless directing groups, overcoming limitations of existing synthetic pathways.