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

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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.

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

You might also read

Related Articles

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

Sort by

Same author

Global patterns of C<sub>3</sub>/C<sub>4</sub> grass biomass allocation: how aridity mediates nitrogen-induced divergent strategies.

The New phytologist·2026

Same author

Simultaneous Determination and Enantiomeric Separation of Five DL-Thiol Compounds Using UHPLC-HRMS With Chiral Derivatization in Sake: Dynamic Monitoring of Human Urine After Drinking.

Chirality·2026

Same author

Bioengineered titanium implants functionalized with aptamer-valproic acid conjugates orchestrate macrophage programming and mesenchymal stem cell homing for improved osseointegration.

Bioactive materials·2026

Same author

A Wearable Thermoelectric Respiratory Sensing System for Quantitative Pulmonary Function Monitoring.

ACS nano·2026

Same author

Nitrogen-Mediated Lanthanide Electronic Perturbations Boost Oxygen Spillover on Nickel-Iron Electrocatalysts for Ultralong-Lifetime Oxygen Evolution.

Nano letters·2026

Same author

Genetic analysis of biopsy-related droplets in patients undergoing PGT-A and its potential application.

Frontiers in endocrinology·2026

Search research articles

Related Experiment Video

Updated: Apr 16, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Modular C-H functionalization cascade of aryl iodides.

Hang Shi¹, David J Babinski¹, Tobias Ritter¹

¹Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society

|March 13, 2015

Summary

This study introduces ipso-borylation for aryl iodides, enabling versatile 1,2-bisfunctionalization. This C-H functionalization method efficiently creates diverse carbon-carbon, carbon-nitrogen, carbon-oxygen, and carbon-halogen bonds.

More Related Videos

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Related Experiment Videos

Last Updated: Apr 16, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Aryl iodides are versatile precursors in organic synthesis.
Efficient methods for 1,2-bisfunctionalization of aryl iodides are crucial for complex molecule synthesis.

Purpose of the Study:

To develop a novel method for the modular 1,2-bisfunctionalization of aryl iodides.
To establish ipso-borylation as a key strategy for accessing diverse functional groups.

Main Methods:

Utilizing C-H functionalization to achieve ipso-borylation of aryl iodides.
Employing the resulting carbon-boron bond as a versatile intermediate.

Main Results:

Demonstrated the first example of ipso-borylation for aryl iodide functionalization.
Successfully synthesized various carbon-carbon, carbon-nitrogen, carbon-oxygen, and carbon-halogen bonds.
Achieved modular synthesis of pharmaceuticals Abilify and Flunixin.

Conclusions:

Ipso-borylation provides a powerful and modular approach for 1,2-bisfunctionalization of aryl iodides.
The developed methodology offers a streamlined route to complex organic molecules and pharmaceuticals.