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

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.2K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.2K
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
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

8.0K
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.
8.0K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

10.2K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
10.2K
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
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

17.9K
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.
17.9K

You might also read

Related Articles

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

Sort by
Same author

Catalytic synthesis of saturated azacycles using transborylation.

Organic & biomolecular chemistry·2026
Same author

Homoconjugation-induced enhancements of photophysical properties in donor-acceptor triptycenes arise from interplay between intramolecular charge transfer and exciton states.

Chemical science·2026
Same author

Ultrathin polymer membranes with locked intrinsic microporosity for hydrocarbon fractionation.

Science (New York, N.Y.)·2026
Same author

Vitamin C appears harmful in patients after out-of-hospital cardiac arrest treated in the intensive care unit.

Intensive care medicine·2026
Same author

Limiting neurodegeneration in ALS: A phosphatase paves the way.

Neuron·2026
Same author

Mitochondria limit coenzyme Q export under cholesterol biosynthetic stress.

The Journal of cell biology·2026
Same journal

Bi-modified Ni<sub>3</sub>S<sub>2</sub> promotes selective nitrite-to-hydroxylamine reduction for cyclohexanone oxime synthesis.

Chemical communications (Cambridge, England)·2026
Same journal

Cyclable manganese inventory as a mechanistic descriptor for electrolyte design in rechargeable aqueous Zn-MnO<sub>2</sub> batteries.

Chemical communications (Cambridge, England)·2026
Same journal

Cobalt-iron layered double hydroxides with ligand modification for boosting glycerol electrooxidation-assisted hydrogen production.

Chemical communications (Cambridge, England)·2026
Same journal

Beyond the vacuum: modeling the solid-liquid interface for gas-involving electrocatalysis.

Chemical communications (Cambridge, England)·2026
Same journal

Alkaline-earth carbonate-supported Ru for quinoline hydrogenation: enhanced H<sub>2</sub> activation <i>via</i> electronic metal-support interaction.

Chemical communications (Cambridge, England)·2026
Same journal

Mitigating ionic conductivity limitations <i>in operando</i> electrochemical X-ray photoelectron spectroscopy.

Chemical communications (Cambridge, England)·2026
See all related articles

Related Experiment Video

Updated: Jun 13, 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

8.0K

Borane-catalysed C2-selective indole reductive functionalisation.

Kieran Nicholson1, Sarah L McOnie1, Thomas Langer2

  • 1EaStCHEM School of Chemistry, University of Edinburgh David Brewster Road, Edinburgh, EH9 3FJ, UK. stephen.thomas@ed.ac.uk.

Chemical Communications (Cambridge, England)
|September 9, 2024
PubMed
Summary
This summary is machine-generated.

Boron catalysis achieves selective allylation of indoles, yielding allylic indolines with high diastereoselectivity. This method utilizes in situ generated allylic boranes for efficient indole functionalization.

More Related Videos

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.1K

Related Experiment Videos

Last Updated: Jun 13, 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

8.0K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.1K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Indoline structures are prevalent in pharmaceuticals and natural products.
  • Developing efficient synthetic routes to functionalized indolines is crucial for drug discovery.

Purpose of the Study:

  • To develop a chemoselective catalytic method for the synthesis of allylic indolines.
  • To investigate the mechanism of boron-catalyzed indole allylation.

Main Methods:

  • Utilized boron catalysis for the direct allylation of indoles.
  • Employed mechanistic studies including in situ intermediate characterization.

Main Results:

  • Achieved chemoselective allylation of indoles to produce allylic indolines.
  • Demonstrated excellent diastereoselectivity in the allylation reaction.
  • Elucidated the catalytic cycle involving allylic borane formation and transborylation.

Conclusions:

  • Boron catalysis offers a powerful strategy for synthesizing valuable allylic indolines.
  • The mechanistic insights provide a foundation for further catalyst development.