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

VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

40.2K
Effect of Lone Pairs of Electrons on Molecule Geometry
40.2K
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

51.7K
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
51.7K
Exceptions to the Octet Rule02:55

Exceptions to the Octet Rule

31.4K
Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
31.4K
VSEPR Theory and the Basic Shapes02:52

VSEPR Theory and the Basic Shapes

62.1K
Overview of VSEPR Theory
62.1K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

9.1K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
9.1K
Predicting Molecular Geometry02:27

Predicting Molecular Geometry

35.7K
VSEPR Theory for Determination of Electron Pair Geometries
35.7K

You might also read

Related Articles

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

Sort by
Same author

Highly Selective and Modular Assembly of Densely Substituted Tetrahydrofurans.

Journal of the American Chemical Society·2026
Same author

Direct Regioselective para-Fluorination via I(I)/I(III) Catalysis.

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

Anomeric Amide Enabled Divergent Synthesis of Unsymmetrical Ureas, Carbamates, Thioesters, and Amides From Aldehydes.

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

N─H or O─H Bond Activation With a Bicyclic Si<sub>4</sub> Ring Compound.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Accessing Medium-Sized Bridged Heterocycles via EnT-Catalyzed Intermolecular Dearomative (5 + 4) Cycloaddition of Furans and Oxazoles.

Journal of the American Chemical Society·2026
Same author

Energy Transfer-Enabled Photocycloaddition of Oxazino Pyridines with Vinyl Azides to Access <i>Meta</i>-Functionalized Pyridines.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: May 4, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

11.3K

Formylborane formation with frustrated Lewis pair templates.

Muhammad Sajid1, Gerald Kehr, Constantin G Daniliuc

  • 1Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany).

Angewandte Chemie (International Ed. in English)
|December 17, 2013
PubMed
Summary

Researchers achieved a breakthrough in hydroboration by stabilizing formylborane using frustrated Lewis pairs (FLPs). This stable formylborane can then undergo typical carbonyl compound reactions, opening new synthetic pathways.

Keywords:
aldehydesboroncarbon monoxideformylboranesfrustrated Lewis pairs

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

8.5K
Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.1K

Related Experiment Videos

Last Updated: May 4, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

11.3K
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

8.5K
Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.1K

Area of Science:

  • Organoboron Chemistry
  • Frustrated Lewis Pair Chemistry
  • Organic Synthesis

Background:

  • Boranes (R2 BH) typically react with carbon monoxide (CO) to form borane carbonyl compounds (R2 BH(CO)).
  • Subsequent hydroboration of CO onto boranes is usually endothermic, hindering formylborane formation.
  • Piers borane, HB(C6F5)2, is a well-known Lewis acid used in hydroboration reactions.

Purpose of the Study:

  • To investigate the CO-hydroboration of Piers borane under frustrated Lewis pair (FLP) conditions.
  • To synthesize and isolate a stable formylborane derivative.
  • To explore the reactivity of the synthesized formylborane.

Main Methods:

  • Reaction of Piers borane with carbon monoxide in the presence of phosphane/borane FLP templates.
  • Isolation of the intermediate 'η(2) -formylborane'.
  • Liberation of the formylborane using pyridine and subsequent isolation of the stable (pyridine)(C6F5)2BCHO compound.

Main Results:

  • An 'η(2) -formylborane' intermediate was successfully formed via CO-hydroboration using FLP templates.
  • Intact formylborane was liberated from the FLP framework by treatment with pyridine.
  • A stable formylborane compound, (pyridine)(C6F5)2BCHO, was isolated and characterized.
  • The isolated formylborane derivative underwent typical carbonyl compound reactions, including Wittig olefination.

Conclusions:

  • Frustrated Lewis pairs enable the CO-hydroboration of Piers borane, overcoming the endothermicity barrier.
  • Stable formylborane compounds can be synthesized and isolated using this FLP-mediated approach.
  • The synthesized formylborane serves as a versatile building block for further organic transformations.