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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.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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.

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...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

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Related Experiment Video

Updated: Apr 11, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Published on: June 21, 2017

Ruthenium-Catalyzed Acyloin Isomerization via Borrowing Hydrogen.

Jingjing Li¹, Shouang Lan², Jinggong Liu³

¹College of Chemistry, Fuzhou University, Fuzhou350116, China.

The Journal of Organic Chemistry

|April 10, 2026

Summary

Ruthenium catalysts enable efficient acyloin isomerization, yielding valuable α-hydroxyketones. This novel method offers a new pathway for organic synthesis, distinct from traditional mechanisms.

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Area of Science:

Organic Chemistry
Catalysis
Carbohydrate Chemistry

Background:

Acyloin isomerization is crucial in carbohydrate chemistry, biological processes, and organic synthesis.
Developing effective catalytic methods for acyloin isomerization remains a significant challenge in synthetic chemistry.

Purpose of the Study:

To develop a novel ruthenium-catalyzed method for acyloin isomerization.
To explore the mechanism of this catalytic transformation and identify key intermediates.

Main Methods:

Ruthenium-catalyzed reaction of acyloin compounds.
Characterization of reaction products, including α-hydroxyketones.
Mechanistic studies to elucidate the reaction pathway.

Main Results:

Successfully developed a ruthenium-catalyzed acyloin isomerization reaction.
Produced a diverse range of α-hydroxyketones from various substrates.
Proposed a novel reaction mechanism involving a borrowing-hydrogen process and a 1,2-diketone intermediate, differing from the conventional enediol mechanism.

Conclusions:

The developed ruthenium-catalyzed method provides an effective route to α-hydroxyketones.
The proposed borrowing-hydrogen mechanism offers new mechanistic insights into acyloin isomerization.
The α-hydroxyketone products serve as versatile precursors for synthesizing valuable molecules.