Strain-Release-Driven Ring Opening of 3-Alkylideneazetidines To Access β-Halomethyl Allylamines
Abstract
An efficient, strain-driven ring opening of 3-alkylideneazetidines has been developed, enabling the one-step construction of both carbon–halogen and carbon–nitrogen bonds to afford structurally diverse β-halomethyl allylamines. This transformation is initiated by arynes as electrophiles, forming an azetidinium intermediate that undergoes nucleophilic attack by a halide anion to proceed with the ring-opening reaction. The protocol features the advantages of inexpensive and environmentally benign potassium halides as halogen sources, transition-metal-free conditions, and high stereoselectivity ( E / Z ). The utility of the resulting β-halomethyl allylamines was demonstrated by their further transformation into valuable allylamines and potential anti-inflammatory activity in preliminary bioassays.
Fields of Study & Subjects
Synthesis and Catalytic Reactions
Chemical Reactions and Mechanisms
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 19
- Pages
- 6083–6088
- Publication date
- 5 May 2026
- Language
- EN