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

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.5K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.5K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

11.0K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
11.0K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.9K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.9K
The Eukaryotic Promoter Region02:40

The Eukaryotic Promoter Region

19.0K
The eukaryotic promoter region is a segment of DNA located upstream of a gene. It contains an RNA polymerase binding site, a transcription start site, and several cis-regulatory sequences.  The proximal promoter region is located in the vicinity of the gene and has cis-regulatory sequences and the core promoter. The core promoter is the binding site for RNA polymerase and is usually located between -35 and +35 nucleotides from the transcription start site. The distal promoter regions are...
19.0K
The Eukaryotic Promoter Region02:40

The Eukaryotic Promoter Region

4.0K
4.0K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.5K
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.
9.5K

You might also read

Related Articles

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

Sort by
Same author

Structural insights into YheS-mediated release of SecM-arrested ribosome.

Nature communications·2026
Same author

Glucose-Modified Viscosity-Responsive Turn-On Fluorescence Molecular Rotors for Wash-Free Live-Cell Imaging.

Chembiochem : a European journal of chemical biology·2026
Same author

NanoLuc-Driven Multiplex Imaging Platforms Incorporating Novel G-series Coelenterazine Variants.

Bioconjugate chemistry·2026
Same author

Identification of Paramyosin as a Novel Allergen in Edible Cricket Protein.

Journal of nutritional science and vitaminology·2026
Same author

Coelenterazine Analog Library for Specific Imaging of Serum Albumins on Conventional and Paper Microplates.

Bioconjugate chemistry·2026
Same author

Hokuriku-plus Heart Failure Registry Study　- Rationale and Study Design.

Circulation reports·2026

Related Experiment Video

Updated: Feb 16, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.3K

Magnesium-Promoted Benzidine-Type Rearrangement for Regioselective Construction of Polyfunctionalized Biaryls.

Shumpei Saito1, Manato Ishida1, Yuki Busujima1

  • 1Department of Life Science and Technology, School of Life Science and Technology, Institute of Science Tokyo, Yokohama, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 15, 2026
PubMed
Summary

A new magnesium-promoted reaction enables efficient synthesis of 1-amino-1-hydroxy-4,4-biaryls. This method uses a novel substrate design for regioselective benzidine-type rearrangements and access to valuable biaryl compounds.

Keywords:
Grignard reagentsbenzidine‐type rearrangementbenzimidazolesbiarylsnitroarenes

More Related Videos

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

3.5K
Plant Promoter Analysis: Identification and Characterization of Root Nodule Specific Promoter in the Common Bean
10:58

Plant Promoter Analysis: Identification and Characterization of Root Nodule Specific Promoter in the Common Bean

Published on: December 23, 2017

13.1K

Related Experiment Videos

Last Updated: Feb 16, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.3K
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

3.5K
Plant Promoter Analysis: Identification and Characterization of Root Nodule Specific Promoter in the Common Bean
10:58

Plant Promoter Analysis: Identification and Characterization of Root Nodule Specific Promoter in the Common Bean

Published on: December 23, 2017

13.1K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Benzidine-type rearrangements are crucial for synthesizing biaryl compounds.
  • Existing methods often require harsh conditions or transition metals.

Purpose of the Study:

  • To develop a novel, transition-metal-free method for synthesizing 1-amino-1-hydroxy-4,4-biaryls.
  • To explore substrate control for regioselective benzidine-type rearrangements.

Main Methods:

  • Magnesium-promoted benzidine-type rearrangement of 1,3-dihalonitroarenes.
  • Utilized aryl Grignard reagents and specifically designed substrates with ortho and meta substituents.
  • Investigated intramolecular cyclization of trifluoroacetamide-substituted nitroarenes.

Main Results:

  • Achieved highly regioselective and efficient synthesis of 1-amino-1-hydroxy-4,4-biaryls.
  • Demonstrated broad functional-group tolerance and excellent scalability.
  • Successfully synthesized CF3-substituted benzimidazoles via a [5,5]-rearrangement and cyclization pathway.

Conclusions:

  • Established a sustainable and mechanistically tunable strategy for biaryl and heteroaromatic synthesis.
  • Expanded the scope of benzidine-type rearrangements with a novel magnesium-promoted approach.
  • Provided direct access to polyfunctionalized biaryls and valuable heterocyclic compounds.