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

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Electrophilic Addition to Alkynes: Halogenation02:38

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.
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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: Hydrohalogenation02:35

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

You might also read

Related Articles

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

Sort by
Same author

Progress toward a Nonenzymatic Gluconeogenesis: One-Pot Reactions and Model Systems.

JACS Au·2026
Same author

A Nonenzymatic Analogue of the Biosynthesis of Pyridoxal Vitamers.

Journal of the American Chemical Society·2026
Same author

Shadow metabolism at interfaces.

Nature chemical biology·2026
Same author

A tertiary amine synthesis <i>via</i> a hydroxylamine alkylation/catalytic reduction sequence.

Organic & biomolecular chemistry·2026
Same author

Correction to "Cope-Type Hydroamination of Vinylboronates".

Organic letters·2025
Same author

High-throughput evaluation of novel WRN inhibitors.

SLAS discovery : advancing life sciences R & D·2025
Same journal

Concise Synthesis of Pyrano/Benzopyrano[2,3-<i>c</i>]pyrazol-6-ones via Ir/Rh-Catalyzed C-H Activation and Tandem Annulation.

The Journal of organic chemistry·2026
Same journal

Regiodivergent Cyclizations of Donor-Acceptor Cyclopropanes with Hydrazines under Solventless, Mechanochemical Milling.

The Journal of organic chemistry·2026
Same journal

Photocatalytic Decarboxylative Coupling of Diacyl Peroxides with TEMPO.

The Journal of organic chemistry·2026
Same journal

Mechanistic Insights into the Isothiourea-Catalyzed Addition Reaction of a <i>para</i>-Nitrophenyl Ester and an <i>N</i>-Benzylpyridinium Salt.

The Journal of organic chemistry·2026
Same journal

Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Anthrones and 9-Phenanthrols.

The Journal of organic chemistry·2026
Same journal

Copper(II)-Catalyzed <i>N</i>-Arylation and <i>N</i>-Vinylation of Oxadiazolones with Boronic Acids under Mild Conditions.

The Journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: Jul 8, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Intermolecular hydroaminations via strained (E)-cycloalkenes.

Joseph Moran1, Pamela H Cebrowski, André M Beauchemin

  • 1Department of Chemistry, Centre for Catalysis Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.

The Journal of Organic Chemistry
|December 29, 2007
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel photoinduced procedure for intermolecular hydroamination of alkenes using azoles. This method efficiently synthesizes complex Markovnikov adducts from cyclic alkenes and various azoles.

More Related Videos

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Related Experiment Videos

Last Updated: Jul 8, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Intermolecular hydroamination of alkenes is a crucial transformation in organic synthesis.
  • Developing efficient and versatile methods for alkene functionalization remains an active area of research.
  • Azoles are important heterocyclic compounds with diverse applications.

Purpose of the Study:

  • To describe a novel photoinduced intermolecular hydroamination of alkenes using azoles.
  • To explore the scope and limitations of this new synthetic method.
  • To elucidate the proposed reaction mechanism.

Main Methods:

  • Irradiation of alkenes with azoles at 254 nm.
  • Use of methyl benzoate as a photosensitizer.
  • Inclusion of triflic acid as an additive.
  • Analysis of reaction products using standard organic chemistry techniques.

Main Results:

  • The reaction proceeds in modest to good yields for 6- and 7-membered cyclic alkenes.
  • A range of azoles, including imidazoles, pyrazoles, triazoles, and tetrazoles, can be employed.
  • Complex Markovnikov adducts are formed.
  • Alkene isomerization was identified as a competing side reaction.

Conclusions:

  • A new photoinduced intermolecular hydroamination of alkenes with azoles has been established.
  • The method offers a valuable route to functionalized cyclic alkenes.
  • The proposed mechanism involves photoisomerization and subsequent nucleophilic attack by the azole.