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

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

7.8K
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.
7.8K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.0K
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...
8.0K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

2.7K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
2.7K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

17.8K
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.
17.8K
Halogenation of Alkenes02:46

Halogenation of Alkenes

15.2K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.4K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.4K

You might also read

Related Articles

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

Sort by
Same author

Formal nitrogen-to-carbon replacement in isoindolines to form indenes <i>via N</i>-alkyl tetrahydroisoquinolines.

Chemical science·2026
Same author

Energy-Transfer Catalysis Enables the Birch-Type Reduction of 2-Pyridones.

Angewandte Chemie (International ed. in English)·2026
Same author

Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.

Journal of the American Chemical Society·2026
Same author

Higher-Level Strategies for Computer-Aided Retrosynthesis.

ACS central science·2026
Same author

An "Inside-Out" Strategy Enables a 14-Step Total Synthesis of Hispidospermidin.

JACS Au·2026
Same author

Unified Total Synthesis of <i>C</i><sub>2</sub>-Symmetric Bis(cyclotryptamine) Alkaloids Utilizing a Single-Atom Insertion/Deletion Strategy.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: May 25, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

7.9K

Two-Step Constitutional Isomerization of Saturated Cyclic Amines Using Borane Catalysis.

Charis Amber1, Timothée M Petitjean1, Giedre Sirvinskaite1

  • 1Department of Chemistry, University of California, Berkeley, California 94720, United States.

JACS Au
|February 28, 2025
PubMed
Summary

Researchers developed a new borane-catalyzed reaction to rearrange saturated nitrogen-containing rings (azacycles). This method efficiently alters molecular structures without changing their formula, enabling access to novel chemical compounds for drug discovery.

More Related Videos

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

2.6K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

6.8K

Related Experiment Videos

Last Updated: May 25, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

7.9K
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

2.6K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

6.8K

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Saturated azacycles are prevalent in pharmaceuticals and natural products.
  • Methods for modifying azacycle periphery are abundant, but core interconversions are limited.
  • Existing core modification methods require extra steps or specific substrates, hindering drug discovery.

Purpose of the Study:

  • To develop a novel method for interconverting saturated azacyclic frameworks.
  • To enable access to underexplored chemical space.
  • To provide a general platform for saturated amine constitutional isomerization.

Main Methods:

  • Borane-catalyzed reductive Stieglitz-type contraction of saturated N-hydroxy azacycles.
  • Investigation of reaction mechanism using density functional theory.

Main Results:

  • A novel transformation enabling reorganization of azacyclic connectivity without altering molecular formula.
  • Products generated without vestigial functionality from auxiliary groups.
  • Demonstrated rapid late-stage reorganization of bioactive molecules.

Conclusions:

  • A general platform for saturated amine constitutional isomerization has been achieved.
  • The method facilitates access to novel chemical entities.
  • The reaction is enabled by a key stereoelectronic interaction.