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

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.9K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.7K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.8K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.5K
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...
6.5K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.1K

You might also read

Related Articles

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

Sort by
Same author

Isostructural Perylene Diimide-Based Metal-Organic Frameworks for Efficient Photocatalytic Oxidation of Benzylamines.

Inorganic chemistry·2026
Same author

Transient Directing Group-Enabled Palladium-Catalyzed Axially Chiral C-H Alkynylation.

Organic letters·2026
Same author

Precise Editing of Indolines at Different Positions via SET and CMD Pathways.

JACS Au·2026
Same author

Tetraphenylethylene-Imidazole-Based MOFs for Broad Spectrum and Chain-Length Complementary Detection of Polyfluoroalkyl Substances.

Inorganic chemistry·2026
Same author

High-Efficient Photocatalytic Synthesis of Tetrahydroquinolines Featuring Cu/Zr Metal-Organic Frameworks.

ACS applied materials & interfaces·2026
Same author

Regioselective Co(III)-Catalyzed C-H Functionalization of 2-Pyridones with Allenes.

Organic letters·2025

Related Experiment Video

Updated: Sep 25, 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

8.1K

Mild Three-Step Consecutive C-H Activations.

Yao-Yao Liu1, Yuan-Lu Qu1, Yan-Shang Kang1

  • 1Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Collaborative Innovation Center of Advanced Micro-structures, Nanjing University, Nanjing 210023, China.

Organic Letters
|April 27, 2022
PubMed
Summary

A new Rh-catalyzed cascade reaction efficiently constructs pharmaceutical derivatives. This triple C-H activation method operates under mild conditions, showcasing high reactivity and low catalyst loading for broad applicability.

More Related Videos

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

14.0K
Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
11:17

Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction

Published on: January 19, 2016

22.1K

Related Experiment Videos

Last Updated: Sep 25, 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

8.1K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

14.0K
Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
11:17

Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction

Published on: January 19, 2016

22.1K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • C-H activation is a powerful tool in organic synthesis.
  • Cascade reactions offer efficient pathways to complex molecules.
  • Developing new catalytic systems for C-H functionalization is crucial.

Purpose of the Study:

  • To develop a novel Rh-catalyzed cascade reaction for constructing pharmaceutical derivatives.
  • To investigate the regioselectivity of C-H activation in a consecutive olefination/annulation/olefination process.
  • To achieve this transformation under mild conditions with high efficiency.

Main Methods:

  • Utilized a rhodium (Rh) catalyst for a consecutive C-H bond olefination/annulation/olefination cascade.
  • Employed sulfonamide and ester groups as directing groups.
  • Assisted the reaction with 1-adamantane carboxylic acid under mild conditions (50 °C).

Main Results:

  • Successfully developed a Rh-catalyzed triple C-H activation cascade.
  • Demonstrated preference for a seven-membered metallacycle over a five-membered one during the third C-H activation.
  • Achieved high reactivity with low catalyst loading.
  • Showcased the method's applicability in synthesizing diverse pharmaceutical derivatives.

Conclusions:

  • The developed Rh-catalyzed cascade reaction provides an efficient route to complex molecules.
  • The reaction proceeds under mild conditions with high catalytic efficiency.
  • This methodology holds significant potential for pharmaceutical synthesis and drug discovery.