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Updated: Jun 1, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Strain-promoted azide-alkyne cycloaddition enhanced by secondary interactions
Riko Yoshikawa1, Shohei Hamada1, Jun-Ichi Matsuo1
1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp.
This study shows that secondary interactions accelerate azide-alkyne cycloaddition reactions. These interactions also control regioselectivity, leading to triazole formation with boronate ester groups.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Azide-alkyne cycloaddition is a key reaction in click chemistry.
- Controlling regioselectivity and reaction rates remains a challenge.
Purpose of the Study:
- To investigate the role of secondary interactions in azide-alkyne cycloaddition.
- To explore the formation of triazoles with boronate ester functionalities.
Main Methods:
- Conducted azide-alkyne cycloaddition between cyclooct-2-yn-1-ol and 2-(azidophenyl)boronic acid.
- Analyzed the reaction kinetics and regioselectivity.
- Evaluated potential imine or hemiaminal interactions.
Main Results:
- The reaction proceeded rapidly at room temperature with complete regioselectivity.
- A triazole with a boronate ester group was successfully synthesized.
- Secondary interactions forming a boronate ion were identified as key factors for rate acceleration and regioselectivity control.
Conclusions:
- Secondary interactions, particularly boronate ion formation, significantly enhance azide-alkyne cycloaddition.
- This work provides insights into controlling complex cycloaddition reactions for targeted synthesis.
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