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

Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is stabilized by...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...

You might also read

Related Articles

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

Sort by
Same author

Catalyst-controlled site-selective dehydrogenation, a stepping stone for C-H oxidations in complex terpenes synthesis.

Nature communications·2026
Same author

Conformation-driven C3-C(<i>sp</i> <sup>3</sup>)-H arylation of saturated azacycles using Pd catalyst.

Nature catalysis·2026
Same author

Pd(II)-Catalyzed Oxidative Annulation of Alkenes toward Isoxazoline <i>N</i>-Oxides.

Organic letters·2026
Same author

Ligand-Enabled Stereoselective Coupling of Methylene C(sp<sup>3</sup>)─H Bonds With Alkenyl Bromide via Pd<sup>II</sup>/Pd<sup>0</sup>/Pd<sup>II</sup> Catalysis.

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

Ni(DQ)<sub>2</sub>: A Useful Gateway to Zero-Valent Nickel Complexes.

Organometallics·2026
Same author

Ligand-Enabled Ag-Free Cross-Coupling of Methylene C(sp<sup>3</sup>)-H Bonds in Aliphatic Acids with C(sp<sup>2</sup>) Bromides.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: May 26, 2026

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

Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Keary M Engle1, Tian-Sheng Mei, Masayuki Wasa

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Accounts of Chemical Research
|December 15, 2011
PubMed
Summary

This study explores palladium-catalyzed C-H functionalization, focusing on using existing functional groups to direct reactions. This approach enables efficient synthesis of complex molecules by activating otherwise inert carbon-hydrogen bonds.

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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Related Experiment Videos

Last Updated: May 26, 2026

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

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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-hydrogen (C-H) bond functionalization offers novel synthetic routes but faces challenges in selectivity and substrate scope.
  • Homogeneous transition metal-catalyzed C-H functionalization is broadly divided into 'first functionalization' (unactivated hydrocarbons) and 'further functionalization' (pre-functionalized substrates).
  • Further functionalization leverages existing groups for catalyst coordination, enhancing reactivity and selectivity, ideally using intrinsic functional groups to avoid extra synthetic steps.

Purpose of the Study:

  • To investigate the use of commonly occurring functional groups as weak coordinating directing groups in palladium-catalyzed C-H functionalization.
  • To develop efficient and selective synthetic methods for the further functionalization of complex organic molecules.
  • To explore the scope and limitations of this approach with diverse substrates and coupling partners.

Main Methods:

  • Focus on palladium-catalyzed reactions utilizing weak coordination of intrinsic functional groups to direct C-H bond cleavage.
  • Development and optimization of reaction conditions to achieve high chemo- and site-selectivity.
  • Application of the developed methodology to a range of substrates and coupling partners.

Main Results:

  • Demonstrated successful palladium-catalyzed C-H functionalization reactions directed by weakly coordinating functional groups.
  • Achieved broad substrate scope and high reactivity, attributed to the formation of reactive cyclopalladated intermediates.
  • Developed a powerful strategy for increasing molecular complexity in a single synthetic step.

Conclusions:

  • Weakly coordinating functional groups can effectively direct palladium-catalyzed C-H functionalization, enabling efficient synthesis.
  • This approach offers a valuable tool for organic chemists, expanding the possibilities of retrosynthetic analysis.
  • The high reactivity of cyclopalladated intermediates facilitates diverse transformations and broad applicability.