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

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.6K
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.
20.6K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

4.9K
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
4.9K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.3K
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.
9.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

9.6K
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
9.6K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

7.1K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
7.1K

You might also read

Related Articles

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

Sort by
Same author

Carbonylative Aminative Suzuki-Miyaura Coupling: Pd-Catalyzed Synthesis of Amides from Vinyl/Aryl Halides and Boronic Acids.

Journal of the American Chemical Society·2026
Same author

Mapping the crystallization landscape of rare earth MOFs: a high-throughput investigation of structure, kinetics, and selectivity.

Chemical science·2026
Same author

Deep integration of clinical metadata with [<sup>18</sup>F]FDG PET/CT imaging for histological subtyping in non-small cell lung cancer: a multi-center study.

European journal of nuclear medicine and molecular imaging·2026
Same author

Quantitative prediction of siRNA complexation by ionizable drugs enables their codelivery in nanoparticles.

Science advances·2026
Same author

A high-resolution dataset on costs and greenhouse gas emissions of battery recycling in China.

Scientific data·2026
Same author

Case Report: Robotic-assisted resection of intra-abdominal aggressive fibromatosis and Boari flap ureteroneocystostomy for hydronephrosis.

Frontiers in oncology·2026

Related Experiment Video

Updated: Jan 11, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.8K

Bulky Phosphine Ligands Promote Palladium-Catalyzed Protodeboronation.

Cher Tian Ser1,2, Han Hao1,3, Sergio Pablo-García1,2,3

  • 1Chemical Physics Theory Group, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

Journal of the American Chemical Society
|November 17, 2025
PubMed
Summary
This summary is machine-generated.

Protodeboronation, a side reaction in Suzuki-Miyaura cross-coupling, is accelerated by palladium catalysts with bulky phosphine ligands. These ligands, often used to aid difficult couplings, can paradoxically hinder product formation.

More Related Videos

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

8.2K
Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles
11:54

Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles

Published on: June 25, 2018

10.7K

Related Experiment Videos

Last Updated: Jan 11, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.8K
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

8.2K
Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles
11:54

Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles

Published on: June 25, 2018

10.7K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • The Suzuki-Miyaura cross-coupling reaction is a vital synthetic tool in organic chemistry.
  • Protodeboronation, the hydrolysis of boronic acid derivatives, is a significant side reaction that reduces the efficiency of Suzuki-Miyaura couplings.
  • While base-catalyzed protodeboronation is well-studied, the role of palladium-phosphine catalysts in this process remains less understood.

Purpose of the Study:

  • To investigate the mechanistic pathways of protodeboronation catalyzed by palladium-phosphine complexes.
  • To determine the influence of ligand structure, particularly bulky phosphines, on the rate of protodeboronation.
  • To provide insights for optimizing Suzuki-Miyaura reaction conditions and ligand selection.

Main Methods:

  • Utilized automated high-throughput experimentation to screen reaction conditions and catalyst systems.
  • Performed comprehensive computational mechanistic analyses to elucidate reaction pathways.
  • Employed kinetic modeling to quantify reaction rates and identify rate-determining steps.

Main Results:

  • Demonstrated that palladium(II) complexes featuring bulky phosphine ligands significantly accelerate protodeboronation.
  • Identified a paradoxical effect where sterically hindered ligands, typically beneficial for cross-coupling, can impede product formation by promoting protodeboronation.
  • Quantified the kinetic impact of ligand bulk on both catalytic cycles.

Conclusions:

  • Bulky phosphine ligands, while often employed to enhance Suzuki-Miyaura cross-coupling efficiency, can inadvertently promote protodeboronation.
  • Careful selection of phosphine ligands is crucial to mitigate protodeboronation and maximize product yield in Suzuki-Miyaura reactions.
  • This study provides critical mechanistic understanding for the rational design of catalysts and optimization of reaction conditions for Suzuki-Miyaura cross-couplings.