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

8.4K
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.
8.4K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.5K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.3K
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.
18.3K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.2K
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...
8.2K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.3K
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...
6.3K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.9K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
9.9K

You might also read

Related Articles

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

Sort by
Same author

Identification of Potential Roles of Bestrophin 3 in the Growth Performance of Ortiental River Prawn <i>Macrobrachium nipponense</i> by RNA Interference.

International journal of molecular sciences·2026
Same author

Development and Validation of Machine-Learning-Based Prediction Models for Thyroid Diseases During Pregnancy.

Medical science monitor : international medical journal of experimental and clinical research·2026
Same author

Outside-in foraminal access for cervical dumbbell tumors: a surgical paradigm shift with technical insights and clinical outcomes.

Journal of neurosurgery. Spine·2026
Same author

Molecular engineering of a 2,5-dithiophen-2-yl-pyrrole-bridged terpyridine-Fe(II) coordination polymer toward multi-state electrochromic energy storage.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Variations in Plankton Community Structure Between Freshwater and Saline-Alkaline Waters and Their Correlation with Nutrient Composition in <i>Macrobrachium nipponense</i>.

Animals : an open access journal from MDPI·2026
Same author

Glioma-related epilepsy in patients with oligodendroglioma, IDH-mutant, and 1p/19q-codeleted: A single-institute study.

Epileptic disorders : international epilepsy journal with videotape·2026

Related Experiment Video

Updated: Jul 22, 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

A Versatile Route to Acyl (MIDA)Boronates.

Hui Qiao1, Jean Michalland1, Qi Huang1

  • 1Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole polytechnique, 91128, Palaiseau Cedex, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 21, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method using acetyl (MIDA)boronate radicals to create complex molecules. This approach offers a versatile route to novel compounds, including precursors for substituted pyrroles and furans.

Keywords:
acyl (MIDA)boronatesfuranspyrrolesradical additionxanthates

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

2.8K
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.3K

Related Experiment Videos

Last Updated: Jul 22, 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 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

2.8K
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.3K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Boron Chemistry

Background:

  • Acyl (MIDA)boronates are valuable synthetic intermediates.
  • Generation and reactivity of acetyl (MIDA)boronate radical were previously unexplored.
  • Existing synthetic methods have limitations in accessing certain functionalized structures.

Purpose of the Study:

  • To describe a novel modular approach for synthesizing highly functional acyl (MIDA)boronates.
  • To introduce a new radical intermediate derived from acetyl (MIDA)boronate.
  • To demonstrate the utility of this radical in carbon-carbon bond formation with unactivated alkenes.

Main Methods:

  • Generation of a novel radical from acetyl (MIDA)boronate using an α-xanthyl precursor.
  • Radical capture reactions with various alkenes, including unactivated substrates.
  • Transformation of resulting products into B(MIDA) substituted pyrroles and furans.

Main Results:

  • The acetyl (MIDA)boronate radical was successfully generated and shown to be well-behaved in synthesis.
  • The method provides access to previously inaccessible structures, such as latent 1,4-dicarbonyl derivatives.
  • Competition experiments revealed the radical's stability relative to other carbon-centered radicals.

Conclusions:

  • The novel α-xanthyl acetyl (MIDA)boronate serves as a convenient and shelf-stable transfer agent.
  • This modular approach expands the synthetic utility of acyl (MIDA)boronates.
  • The methodology enables the efficient synthesis of diverse molecular architectures.