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Updated: Aug 11, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper(I)-Catalyzed Alkyne-Azide Cycloaddition (CuAAC) "Click" Reaction: A Powerful Tool for Functionalizing
Héctor Manuel Pineda-Castañeda1, Zuly Jenny Rivera-Monroy1, Mauricio Maldonado1
1Chemistry Department, Universidad Nacional de Colombia, Bogotá, Carrera 45 No 26-85, Building 451, office 409, Bogotá 11321, Colombia.
Click chemistry, particularly copper-catalyzed azide-alkyne cycloaddition (CuAAC), offers efficient synthesis of complex organic molecules. This review highlights its application on polyhydroxylated platforms like resorcinarenes and calixarenes.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Click chemistry is a powerful synthetic tool for creating complex organic molecules.
- Its advantages include mild conditions, high yields, and short reaction times, making it ideal for efficient synthesis.
Purpose of the Study:
- This review focuses on the application of click chemistry, specifically copper-catalyzed azide-alkyne cycloaddition (CuAAC), for modifying polyhydroxylated platforms.
- The main goal is to detail the synthetic conditions, reagents, and methodologies employed.
Main Methods:
- The review emphasizes the use of copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions.
- Specific focus is placed on the synthesis of modified resorcinarenes and calixarenes.
Main Results:
- CuAAC reactions provide an effective route for the functionalization of polyhydroxylated platforms.
- The methodologies discussed allow for the generation of complex and conjugated molecules.
Conclusions:
- Click chemistry, especially CuAAC, is a highly effective strategy for synthesizing complex molecules on polyhydroxylated scaffolds.
- This approach offers a viable alternative for creating advanced organic structures with desirable properties.
Related Concept Videos
Cycloaddition Reactions: Overview
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

