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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...

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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...

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.

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Updated: Jan 10, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Ruthenium Bis-Sulfonate Complexes: Synthesis and Application in Asymmetric Hydrogenation.

Yifei Zhou^1,2, Pim Vink^1,2, Ibrahim Kılınç¹

¹Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, Wageningen, 6708 WE, The Netherlands.

Organometallics

|November 28, 2025

Summary

Ruthenium complexes with varying anions (OMs, OTs, OTf) were synthesized. Ru-(BINAP)-(OMs)2 demonstrated superior performance in asymmetric hydrogenation compared to the acetate catalyst.

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Published on: April 10, 2015

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Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Published on: October 26, 2017

Area of Science:

Organometallic Chemistry
Catalysis

Background:

Ruthenium complexes are vital catalysts in asymmetric synthesis.
Anion choice significantly influences catalyst activity and selectivity.

Purpose of the Study:

To synthesize and characterize novel Ruthenium-(L)-(X)2 complexes.
To investigate the effect of different anions (X = OMs, OTs, OTf) on catalytic performance.

Main Methods:

Synthesis of Ruthenium complexes with bidentate ligands (L) and various anions (X).
Characterization using standard analytical techniques.
Evaluation of catalytic activity in asymmetric hydrogenation reactions.

Main Results:

Successful synthesis and characterization of Ru-(L)-(X)2 complexes.
Ru-(BINAP)-(OMs)2 exhibited enhanced catalytic performance.
Demonstrated the significant impact of anion variation on hydrogenation outcomes.

Conclusions:

Anion modification is a key strategy for optimizing Ruthenium-catalyzed asymmetric hydrogenations.
The methanesulfonate (OMs) anion offers advantages over acetate (OAc) in this system.