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

8.2K
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.
8.2K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.1K
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...
8.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.1K
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.
18.1K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
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...
4.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
7.7K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.3K

You might also read

Related Articles

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

Sort by
Same author

Functional architecture of cardiac TF regulatory landscapes in control of mammalian heart development.

bioRxiv : the preprint server for biology·2026
Same author

NMR Spectroscopy for Studying the Selective Etching of Ti<sub>3</sub>AlC<sub>2</sub> to Ti<sub>3</sub>C<sub>2</sub>T<sub>x</sub> MXene Using Hexafluorosilicic Acid.

Small methods·2026
Same author

Recent developments in the synthesis and synthetic applications of borane-amines.

Chemical communications (Cambridge, England)·2025
Same author

The efficacy of sodium hexafluoroaluminate (cryolite) for direct amidation of carboxylic acids.

RSC advances·2025
Same author

Rapid, Room-Temperature Amidation via Tandem Titanium Amido Complex and Titanium Carboxylate Intermediates.

Organic letters·2025
Same author

A multi-hospital, clinician-initiated bacterial genomics programme to investigate treatment failure in severe Staphylococcus aureus infections.

Nature communications·2025
Same journal

RETRACTED: Atta et al. Effect of Montmorillonite Nanogel Composite Fillers on the Protection Performance of Epoxy Coatings on Steel Pipelines. <i>Molecules</i> 2017, <i>22</i>, 905.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Chen et al. Chemical Composition of <i>Litsea pungens</i> Essential Oil and Its Potential Antioxidant and Antimicrobial Activities. <i>Molecules</i> 2023, <i>28</i>, 6835.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Ruan et al. Comparison of Extraction, Isolation, Purification, Structural Characterization and Immunomodulatory Activity of Polysaccharides from Two Species of <i>Cistanche</i>. <i>Molecules</i> 2025, <i>30</i>, 4754.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Li et al. Gastrodin Ameliorates Cognitive Dysfunction in Vascular Dementia Rats by Suppressing Ferroptosis via the Regulation of the Nrf2/Keap1-GPx4 Signaling Pathway. <i>Molecules</i> 2022, <i>27</i>, 6311.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Zueva et al. Steady-State Kinetics of Enzyme-Catalyzed Hydrolysis of Echothiophate, a P-S Bonded Organophosphorus as Monitored by Spectrofluorimetry. <i>Molecules</i> 2020, <i>25</i>, 1371.

Molecules (Basel, Switzerland)·2026
Same journal

1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications.

Molecules (Basel, Switzerland)·2026
See all related articles

Related Experiment Video

Updated: Jul 5, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.2K

Borane-Pyridine: An Efficient Catalyst for Direct Amidation.

P Veeraraghavan Ramachandran1, Aman Singh1, Harry Walker1

  • 1Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA.

Molecules (Basel, Switzerland)
|January 11, 2024
PubMed
Summary
This summary is machine-generated.

Borane-pyridine efficiently catalyzes direct amidation reactions, forming carboxamides from diverse carboxylic acids and amines. This liquid catalyst demonstrates excellent solubility and functional group tolerance, simplifying amide synthesis.

Keywords:
borane-aminesborane-pyridinecarboxamidescatalysisdirect amidationliquid catalyst

More Related Videos

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.3K
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

9.7K

Related Experiment Videos

Last Updated: Jul 5, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.2K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.3K
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

9.7K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Direct amidation offers a streamlined route to carboxamides, crucial functional groups in pharmaceuticals and materials.
  • Existing amidation methods often require harsh conditions or pre-activation steps.
  • Developing efficient, mild catalytic systems for direct amidation remains a key challenge.

Purpose of the Study:

  • To introduce borane-pyridine as a highly effective liquid catalyst for direct amidation.
  • To demonstrate the broad substrate scope and functional group tolerance of this catalytic system.
  • To provide a simplified and efficient method for synthesizing secondary and tertiary carboxamides.

Main Methods:

  • Utilizing borane-pyridine (5 mol%) as a liquid catalyst.
  • Reacting a wide range of aromatic and aliphatic carboxylic acids with various amines.
  • Analyzing reaction products for yield and purity.

Main Results:

  • Achieved efficient direct amidation of diverse carboxylic acids and amines.
  • Successfully synthesized secondary and tertiary carboxamides.
  • Demonstrated excellent catalyst solubility and tolerance to halo, nitro, and alkene functionalities.

Conclusions:

  • Borane-pyridine is a versatile and efficient catalyst for direct carboxamide synthesis.
  • The method offers improved solubility and broad functional group compatibility.
  • This approach provides a valuable tool for constructing complex amide structures.