ArticleAngewandte Chemie (International ed. in English)2022
Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed.
- Nucleophilic Substitution of 1,3-Diiodobicyclo[1.1.1]pentane: Synthesis of Bicyclo[1.1.1]pentylpyridinium, Quinolinium, Isoquinolinium, and Pyrazolium Salts.The Journal of organic chemistry · 2025Article
- Modular access to saturated bioisosteres of anilines via photoelectrochemical decarboxylative C(spNature communications · 2025Article
- Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations.Nature synthesis · 2024Article
- Bicyclopentylation of Alcohols with Thianthrenium Reagents.Journal of the American Chemical Society · 2023Article
- 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring.Nature chemistry · 2023Article
- Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane.Organic letters · 2022Article
- A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes.Angewandte Chemie (International ed. in English) · 2022Article
- Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes.Angewandte Chemie (International ed. in English) · 2022Article
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7 authors.
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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.
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