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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...

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.

Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

Radical Anti-Markovnikov Addition to Alkenes: Overview

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity and Stereochemistry of Hydroboration

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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: Jan 8, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Published on: June 20, 2014

Nickel-catalyzed enantioselective C-H functionalization.

Fei Yao¹, Bing-Feng Shi^1,2,3,4

¹State Key Laboratory of Soil Pollution Control and Safety, Department of Chemistry, Zhejiang University, Hangzhou 310058, China. bfshi@zju.edu.cn.

Chemical Communications (Cambridge, England)

|December 16, 2025

Summary

Recent advances showcase nickel catalysis for enantioselective C-H functionalization, overcoming historical limitations. Innovations in ligand design and mechanistic insights are key to nickel

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Published on: August 16, 2018

Area of Science:

Organometallic Chemistry
Asymmetric Catalysis
Sustainable Chemistry

Background:

Nickel, an abundant 3d metal, offers unique redox properties valuable for catalysis.
Enantioselective C-H activation using nickel lags behind noble metals historically.
Recent progress is driven by ligand design and mechanistic understanding.

Purpose of the Study:

To provide a comprehensive overview of recent advances in nickel-catalyzed enantioselective C-H functionalization.
To highlight innovations in ligand design and mechanistic insights for nickel catalysis.

Main Methods:

Review of recent literature on nickel-catalyzed enantioselective C-H functionalization.
Categorization based on catalytic nickel species: nickel(0) and nickel(II) catalysis.
Discussion of specific ligand systems, including SPO, NHC, BINOL, and Salox.

Main Results:

Significant progress has been achieved in nickel-catalyzed enantioselective C-H functionalization.
Nickel(0) catalysis benefits from specialized ligands like SPO and NHC.
Nickel(II) catalysis effectively employs chiral ligands such as BINOL and Salox.

Conclusions:

Nickel is emerging as a powerful and cost-effective alternative for enantioselective C-H functionalization.
Continued innovation in ligand development and mechanistic studies will further expand nickel's catalytic utility.
This review consolidates recent breakthroughs, paving the way for future research in sustainable asymmetric catalysis.