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 Experiment Videos

The solid-phase Nicholas reaction: scope and limitations.

Natalie Gachkova1, Johan Cassel, Stefanie Leue

  • 1Department of Chemistry and Bioscience, Chalmers University of Technology, SE-41296 Göteborg, Sweden.

Journal of Combinatorial Chemistry
|May 10, 2005
PubMed
Summary
This summary is machine-generated.

Related Concept Videos

You might also read

Related Articles

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

Sort by
Same author

Ruthenium-catalyzed synthesis of tricyclic 1,5-fused 1,2,3-triazole piperazines.

Organic & biomolecular chemistry·2025
Same author

Carbon-carbon bond formation using aromatics from biomass.

Chemical communications (Cambridge, England)·2024
Same author

Synthesis, characterization and computational evaluation of bicyclooctadienes towards molecular solar thermal energy storage.

Chemical science·2022
Same author

Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds.

Chemical communications (Cambridge, England)·2021
Same author

Azulene Functionalization by Iron-Mediated Addition to a Cyclohexadiene Scaffold.

The Journal of organic chemistry·2020
Same author

Palladium Catalyzed Stereoselective Arylation of Biocatalytically Derived Cyclic 1,3-Dienes: Chirality Transfer via a Heck-Type Mechanism.

Organic letters·2020
Same journal

Editorial.

Journal of combinatorial chemistry·2016
Same journal

2000 Reviewers.

Journal of combinatorial chemistry·2016
Same journal

Editorial.

Journal of combinatorial chemistry·2016
Same journal

Editorial.

Journal of combinatorial chemistry·2016
Same journal

Editorial.

Journal of combinatorial chemistry·2016
Same journal

Editorial.

Journal of combinatorial chemistry·2016
See all related articles

Solid-phase synthesis of alpha-substituted alkynes was achieved using a Sonogashira/Nicholas reaction sequence. This optimized method efficiently incorporates diverse nucleophiles, enabling rapid library generation.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Solid-phase synthesis offers advantages in purification and automation for creating chemical libraries.
  • The Sonogashira and Nicholas reactions are powerful tools for carbon-carbon bond formation.

Purpose of the Study:

  • To develop a robust solid-phase synthesis of alpha-substituted alkynes.
  • To explore the scope of nucleophiles applicable in the solid-phase Nicholas reaction.
  • To optimize the sequential Sonogashira/Nicholas reaction for efficient library generation.

Main Methods:

  • Sequential Sonogashira coupling followed by Nicholas reaction on a solid support.
  • Investigation of various carbon, oxygen, nitrogen, sulfur, fluoride, and hydride nucleophiles.

Related Experiment Videos

  • Optimization of reaction conditions including Lewis acid, Sonogashira catalyst, temperature, time, and decomplexation.

    • Main Results:

    • Successful preparation of two libraries of alpha-substituted alkynes.
    • Demonstrated broad scope of nucleophiles for the solid-phase Nicholas reaction.
    • Optimized five-step sequence completed in a single day.

    Conclusions:

    • The developed solid-phase strategy provides an efficient route to diverse alpha-substituted alkynes.
    • This methodology is suitable for rapid library synthesis in drug discovery and chemical biology.