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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
4.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.3K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
9.3K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.4K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.9K
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.
9.9K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.0K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
3.0K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.7K
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.
9.7K

You might also read

Related Articles

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

Sort by
Same author

Regioselective Electrosynthesis of Substituted (deuterated) Pyridines Through Enamine-Iminium Cross-Coupling.

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

Synthesis of Unsymmetrical 4,4'-Bipyridines through Base-Mediated Cross-Coupling between 4-Pyridyl Phosphonium Salts.

Organic letters·2026
Same author

Photocatalytic Strain-Release Transformation of Bicyclo[1.1.0]butanes (BCB) Using Strategically Tuned Covalent Organic Frameworks.

Journal of the American Chemical Society·2025
Same author

Unprecedented Copper/Iron-Cocatalyzed Homocoupling of Propargyl Ethers to Conjugated Benzofurans.

JACS Au·2025
Same author

Stereoselective Electrosynthesis of Imidazolines through Coupling and Ring Restructuring of Alkoxyoxazoles with α-Amino Carbonyls.

Organic letters·2025
Same author

Electrochemical Formal (3 + 2) Cycloaddition/Imidation Cascade: Easy Access to Triazabicyclo-[3.3.0] Scaffolds.

Organic letters·2025

Related Experiment Video

Updated: Mar 18, 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

26.0K

Remote C-H Functionalization by a Palladium-Catalyzed Transannular Approach.

Suman De Sarkar1

  • 1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-, 741246, West Bengal, India. suman.sarkar@iiserkol.ac.in.

Angewandte Chemie (International Ed. in English)
|July 9, 2016
PubMed
Summary

Remote C-H arylation of alicyclic amines is now achievable using palladium catalyst transannular coordination. This method enables late-stage functionalization of complex bioactive molecules for structure-activity relationship studies.

Keywords:
C−H activationalicyclic aminesarylationpalladium

More Related Videos

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

10.3K
Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

10.6K

Related Experiment Videos

Last Updated: Mar 18, 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

26.0K
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

10.3K
Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

10.6K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Late-stage functionalization is crucial for drug discovery and development.
  • Direct C-H arylation offers a more efficient route to complex molecules compared to traditional methods.
  • Alicyclic amines are prevalent scaffolds in many bioactive compounds.

Purpose of the Study:

  • To develop a novel method for the remote C-H arylation of alicyclic amines.
  • To demonstrate the utility of palladium-catalyzed transannular coordination in this transformation.
  • To enable efficient late-stage functionalization of complex bioactive molecules.

Main Methods:

  • Utilized a palladium catalyst for C-H arylation.
  • Employed a directing group strategy to achieve remote functionalization.
  • Investigated the transannular coordination of the palladium catalyst as the key step.

Main Results:

  • Successfully achieved remote C-H arylation of various alicyclic amines.
  • Demonstrated the effectiveness of the directing group in controlling regioselectivity.
  • The transannular coordination of the palladium catalyst was confirmed as the crucial mechanistic feature.

Conclusions:

  • Developed a convenient and effective strategy for remote C-H arylation of alicyclic amines.
  • This methodology facilitates late-stage functionalization, aiding in the exploration of structure-activity relationships.
  • The approach holds significant potential for the synthesis of complex pharmaceutical agents.