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 Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.2K
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 stereochemistry.
9.2K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.7K
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.
10.7K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.4K
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.
20.4K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.7K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
2.7K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

7.1K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
7.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.3K

You might also read

Related Articles

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

Sort by
Same author

Nickel-Catalyzed Boron-Mediated Saturative Trifunctionalization of Alkynes.

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

Facile Synthesis of Gem-Difluoroalkene-Based <i>Bis</i>(silanes) via Copper-Catalyzed Disilylative Defluorination of 1-Chloro-1-trifluoromethylalkenes.

Journal of the American Chemical Society·2026
Same author

Boryl Homolytic Aromatic Substitution Enables Radical Borylation via Inverted B-H Polarity of Hydroborane.

Journal of the American Chemical Society·2026
Same author

Et<sub>3</sub>SiOBpin as a Dual Reagent Enabled Photocatalytic Stereoselective Assembly of Multisubstituted Perfluoroalkyl-boryl Styrenes.

Organic letters·2026
Same author

Iridium-Catalyzed B-H/C-H Dehydrogenative Coupling to Enable Boron-Nitrogen-Embedded Polycyclic Aromatic Hydrocarbons.

Journal of the American Chemical Society·2026
Same author

Organophosphine-Mediated Skeletal Editing Synthesis of Benzo[e][1,3]thiazine-2,4(3<i>H</i>)-diones via Curtius Rearrangement.

The Journal of organic chemistry·2025

Related Experiment Video

Updated: Dec 20, 2025

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

3.3K

Base-promoted domino-borylation-protodeboronation strategy.

Zhijie Kuang1, Kai Yang2, Yao Zhou3

  • 1Institute of Next Generation Matter Transformation, College of Materials Science & Engineering and College of Chemical Engineering at Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. China. qsong@hqu.edu.cn.

Chemical Communications (Cambridge, England)
|May 22, 2020
PubMed
Summary

This study introduces base-promoted domino-borylation-protodeboronation (DBP) strategies for synthesizing multi-borylated compounds. These compounds are versatile precursors for creating diverse boron-containing molecules via selective transformations.

More Related Videos

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

8.3K
Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

9.0K

Related Experiment Videos

Last Updated: Dec 20, 2025

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

3.3K
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

8.3K
Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

9.0K

Area of Science:

  • Organic Chemistry
  • Organoboron Chemistry

Background:

  • Nucleophilic borylation of unsaturated compounds is crucial in organic synthesis.
  • In situ generation of nucleophilic sp2 boron species is enabled by inorganic bases, B2pin2, and methanol.
  • Previous strategies have focused on single borylation events, necessitating further development for multi-borylated compound synthesis.

Purpose of the Study:

  • To document the development of base-promoted domino-borylation-protodeboronation (DBP) strategies.
  • To showcase the synthesis of various multi-borylated compounds using DBP.
  • To highlight the applications of DBP-derived compounds in organic synthesis.

Main Methods:

  • In situ generation of nucleophilic sp2 boron species.
  • Base-promoted reactions of unsaturated compounds with B2pin2 and methanol.
  • Selective protodeboronation of multi-borylated intermediates.

Main Results:

  • Successful construction of diverse multi-borylated compounds, including alkyl 1,2-bis(boronates), gem-diborylalkanes, and 1,1,2-tris(boronates).
  • Demonstration of selective protodeboronation for generating various boron-containing compounds.
  • Establishment of DBP as an efficient strategy for accessing complex organoboron structures.

Conclusions:

  • Base-promoted DBP strategies offer a powerful approach for synthesizing multi-borylated compounds.
  • These strategies provide access to valuable boron-containing molecules through selective transformations.
  • DBP represents a significant advancement in the field of organoboron chemistry and organic synthesis.