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Updated: Oct 4, 2025
04:38
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
3.1K
Strain-release arylations for the bis-functionalization of azetidines
Florian Trauner1, Felix Reiners1, Kodjo-Edmond Apaloo-Messan2
1Department of Chemistry and Pharmacy, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 Munich, Germany. dorian.didier@cup.uni-muenchen.de.
Chemical Communications (Cambridge, England)
|February 2, 2022
Summary
This study introduces a method for creating 3-arylated azetidine intermediates using organometallic addition to azabicyclobutanes. Subsequent N-arylation strategies were also developed for these intermediates.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Azabicyclobutanes are strained ring systems.
- Azetidines are important heterocyclic compounds.
Purpose of the Study:
- To develop a method for synthesizing 3-arylated azetidine intermediates.
- To establish single-pot strategies for N-arylation of azetidines.
Main Methods:
- Addition of nucleophilic organometallic species to in situ generated azabicyclobutanes.
- Strain-release reactions.
- Nucleophilic aromatic substitution (SNAr) reactions.
- Buchwald-Hartwig couplings.
Main Results:
- Selective formation of 3-arylated azetidine intermediates.
- Successful development of single-pot strategies for N-arylation.
- Demonstrated utility of SNAr and Buchwald-Hartwig couplings for N-arylation.
Conclusions:
- The developed method provides efficient access to 3-arylated azetidines.
- Single-pot N-arylation strategies offer streamlined synthesis of functionalized azetidines.
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