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

Prochirality02:05

Prochirality

3.8K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
3.8K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.5K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
2.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

5.9K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
5.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
  1. Home
  3. Research Domains
  5. Chemical Sciences
  7. Inorganic Chemistry
  9. Organometallic Chemistry
  11. C2-axis Chiral 10,10'-bibenzoquinoline Ligands Specifically Partnered With Agotf Enable Catalytic Enantioselective Cyclopropanations Of Diazo Carbonates

C2-Axis Chiral 10,10'-Bibenzoquinoline Ligands Specifically Partnered with AgOTf Enable Catalytic Enantioselective Cyclopropanations of Diazo Carbonates

Wen-Sheng Li1, Hao Fan1,2, Guo Cheng1,2

  • 1Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

The Journal of Organic Chemistry
|June 4, 2025

Related Experiment Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.2K
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

2.9K

View abstract on PubMed

Summary
This summary is machine-generated.

New chiral (R)-10,10′-bibenzoquinoline (R-BBQ) ligands efficiently catalyze enantioselective cyclopropanations. This cost-effective silver catalyst system shows potential for organic light-emitting materials.

Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis
  • Materials Science

Background:

  • Development of chiral ligands is crucial for enantioselective synthesis.
  • Chiral bibenzoquinoline (BBQ) ligands offer unique structural features for catalysis.
  • Silver catalysis provides a cost-effective alternative to noble metals.

Purpose of the Study:

  • To design and synthesize novel C2-axis chiral (R)-bibenzoquinoline (R-BBQ) ligands.
  • To investigate the efficacy of R-BBQ ligands in silver-catalyzed enantioselective cyclopropanation reactions.
  • To explore the potential of R-BBQ ligands in organic light-emitting applications.

Main Methods:

  • Rational design and two-step synthesis of R-BBQ ligands via Combes quinoline synthesis from (R)-1,1'-binaphthalene-2,2'-diamine (BINAM).

Related Experiment Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.2K
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

2.9K
  • Application of Ag(I)-R-BBQ complexes as catalysts for cyclopropanation reactions involving diazo oxindoles, α-arylidene diazo succinimides, and diazo carbonates with aromatic alkenes.
  • Characterization of ligand L1 for photophysical properties, including emission wavelength and thermally activated delayed fluorescence (TADF).

    • Main Results:

    • Successful synthesis of novel R-BBQ ligands with C2-axis chirality and super-conjugated aromatic systems.
    • High enantioselectivities (up to 98% ee) and yields (up to 89%) achieved in the silver-catalyzed cyclopropanation of diazo oxindoles and α-arylidene diazo succinimides.
    • Demonstration of the first silver-catalyzed highly enantioselective cyclopropanation of diazo carbonates.
    • Observation of strong emission at 430 nm and TADF properties for ligand L1, indicating potential as an organic light-emitting material.

    Conclusions:

    • The developed R-BBQ ligands are efficient, stable, cost-effective, and readily available catalysts for asymmetric cyclopropanation.
    • The Ag(I)-R-BBQ system represents a significant advancement in enantioselective cyclopropanation, particularly for diazo carbonates.
    • The observed photophysical properties suggest promising applications of R-BBQ ligands in organic electronics, specifically as organic light-emitting materials.