Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...

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.

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.

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...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

The howler monkey genome provides new insights into the distinctive howling and folivorous adaptations of New World monkeys.

Genome biology·2026

Same author

Reduced salen in a monomeric Fe complex.

Chemical communications (Cambridge, England)·2026

Same author

Stereodivergent C-(Hetero)Aryl Glycosylation by Nickel-Catalyzed Redox-Neutral Cross-Coupling of Glycosyl Sulfonyl Hydrazides.

Angewandte Chemie (International ed. in English)·2026

Same author

Transparent and Low-Voltage-Driven Conductive Nanocomposite Hydrogels for Tunable Optical Lenses.

ACS applied materials & interfaces·2026

Same author

NIR-II Imaging-Guided Phototherapy-Induced Senescence Reprograms Immunosuppressive Tumor Microenvironment for Potent Cancer Immunotherapy.

ACS nano·2026

Same author

Reinforcement learning in linear embedding space unlocks generalizable control across soft robot configurations.

Nature communications·2026

Search research articles

Related Experiment Video

Updated: Jun 24, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Congested C(sp3)-rich architectures enabled by iron-catalysed conjunctive alkylation.

Tong-De Tan^1,2, Juan M I Serviano³, Xiaohua Luo¹

¹Department of Chemistry, National University of Singapore, 4 Science Drive 2, Republic of Singapore, 117544.

Nature Catalysis

|June 10, 2024

Summary

This study introduces a novel iron-catalyzed method for creating complex carbon-carbon bonds using alkyl halides and olefins. This breakthrough enables the synthesis of challenging, sterically hindered molecules previously inaccessible through standard organic synthesis techniques.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Related Experiment Videos

Last Updated: Jun 24, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Transition metal-catalyzed cross-coupling reactions have transformed organic synthesis.
Forming multiple alkyl-alkyl bonds, especially in sterically demanding settings, remains a significant synthetic hurdle.
Existing methods often struggle with regioselectivity and substrate scope for complex alkylations.

Purpose of the Study:

To develop a novel catalytic system for the regioselective formation of C-C bonds.
To enable the synthesis of sterically congested molecules with multiple C(sp3)-rich centers.
To explore new avenues for constructing complex molecular architectures.

Main Methods:

Utilized a simple (terpyridine)iron catalyst for cross-coupling reactions.
Employed sp3-hybridized organohalides and organozinc reagents with olefins.
Investigated regioselectivity and substrate scope through various synthetic transformations.

Main Results:

Achieved regioselective functionalization of olefins with diverse aliphatic groups.
Successfully synthesized a variety of products with congested cores and stereocenters.
Demonstrated access to synthetically challenging C(sp3)-rich molecules, including alicyclic compounds via annulation cascades.

Conclusions:

The developed iron-catalyzed method provides efficient access to valuable, sterically hindered molecules.
The methodology expands the scope of C-C bond formation, particularly for alkyl-alkyl couplings.
Mechanistic studies suggest a radical carbometallation pathway, opening possibilities for further catalytic innovations.