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Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes.
- Source :
- Angewandte Chemie (International ed. in English); vol 61, iss 2, e202111291; 1433-7851
- Publication Year :
- 2022
-
Abstract
- Strategies commonly used for the synthesis of functionalised bicyclo[1.1.1]pentanes (BCP) rely on the reaction of [1.1.1]propellane with anionic or radical intermediates. In contrast, electrophilic activation has remained a considerable challenge due to the facile decomposition of BCP cations, which has severely limited the applications of this strategy. Herein, we report the electrophilic activation of [1.1.1]propellane in a halogen bond complex, which enables its reaction with electron-neutral nucleophiles such as anilines and azoles to give nitrogen-substituted BCPs that are prominent motifs in drug discovery. A detailed computational analysis indicates that the key halogen bonding interaction promotes nucleophilic attack without sacrificing cage stabilisation. Overall, our work rehabilitates electrophilic activation of [1.1.1]propellane as a valuable strategy for accessing functionalised BCPs.
Details
- Database :
- OAIster
- Journal :
- Angewandte Chemie (International ed. in English); vol 61, iss 2, e202111291; 1433-7851
- Notes :
- application/pdf, Angewandte Chemie (International ed. in English) vol 61, iss 2, e202111291 1433-7851
- Publication Type :
- Electronic Resource
- Accession number :
- edsoai.on1367450909
- Document Type :
- Electronic Resource