Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.6K
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...
2.6K
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

1.8K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
1.8K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

8.1K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
8.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.6K
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.
21.6K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.6K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.6K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.8K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
11.8K

You might also read

Related Articles

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

Sort by
Same author

Three-State Electrochiroptical Switches Derived from Chiral Stable Carbenes.

Journal of the American Chemical Society·2026
Same author

Generation of mono(amino)carbenes from <i>N</i>-triftosyl amino hydrazonates with blue light.

Chemical communications (Cambridge, England)·2026
Same author

Organocatalysis promoted by 1,2,3-triazolylidenes (MICs): carbenes which make a difference.

Chemical Society reviews·2025
Same author

Switching mesoionic carbene-organocatalysis from radical to ionic pathway through base-controlled formation of Breslow intermediates <i>versus</i> Breslow enolates.

Chemical science·2025
Same author

A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene.

Journal of the American Chemical Society·2025
Same author

Singlet Carbenes Are Stereoinductive Main Group Ambiphiles.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Mar 1, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

8.0K

Borylenes: An Emerging Class of Compounds.

Michele Soleilhavoup1, Guy Bertrand1

  • 1UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.

Angewandte Chemie (International Ed. in English)
|June 4, 2017
PubMed
Summary

Researchers have isolated stable borylenes, which are boron compounds with unique reactivity. These electron-rich borylenes act as ligands for transition metals, expanding organoboron chemistry.

Keywords:
boroncarbenoids

More Related Videos

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
07:20

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

14.5K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.5K

Related Experiment Videos

Last Updated: Mar 1, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

8.0K
Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
07:20

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

14.5K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.5K

Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry

Background:

  • Free borylenes (R-B:) are typically observed only under extreme conditions (gas phase or low-temperature matrices).
  • Recent advancements have enabled the isolation of stabilized borylene derivatives.

Purpose of the Study:

  • To explore the synthesis and properties of isolable mono- and bis(Lewis base)-stabilized borylenes.
  • To investigate the unique electronic properties and reactivity of these borylene compounds.

Main Methods:

  • Isolation and characterization of novel borylene compounds.
  • Spectroscopic analysis to determine electronic structure and oxidation states.
  • Reactivity studies, including small molecule activation and coordination chemistry.

Main Results:

  • Isolation of stable mono- and bis(Lewis base)-stabilized borylenes with boron in the +I oxidation state.
  • Demonstration that these borylenes are electron-rich, unlike traditional Lewis acidic boranes.
  • Mono(Lewis base)-stabilized borylenes exhibit reactivity mimicking transition metals, acting as boron metallomimics.
  • Bis(Lewis base)borylene adducts function as effective ligands for transition metals.

Conclusions:

  • Stabilized borylenes represent a new class of organoboron compounds with accessible chemistry.
  • Their electron-rich nature and ability to act as ligands open new avenues in coordination chemistry and catalysis.
  • Borylenes offer a unique platform for developing novel boron-based materials and reagents.