ArticleJournal of the American Chemical Society2025
Direct Synthesis of Bicyclo[1.1.1]pentanes by Sequential C═C, C-C Functionalization Reactions.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Enantioselective Synthesis of 2-Oxabicyclo[2.1.1]hexanes and Bicyclo[2.1.1]hexanes via Catalytic Asymmetric Intramolecular Photocycloadditions.Nature communications · 2026Article
- Asymmetric C-H Functionalization of Bicyclo[2.1.1]hexanes and Their 2-Oxa- and 2-Aza Derivatives via Rhodium Carbene Intermediates.Journal of the American Chemical Society · 2026Article
- Propellane-free access to bicyclo[1.1.1]pentanes.Nature communications · 2026Review
- Dibromocarbene addition to bicyclo[1.1.0]butanes: A facile route to substituted bicyclo[1.1.1]pentanes.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Direct Synthesis of Bicyclo[1.1.1]pentanes by Sequential C═C, C-C Functionalization Reactions.Journal of the American Chemical Society · 2025Article
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Authors and funding
4 authors.
Funding
Abstract
2-Substituted bicyclo[1.1.1]pentane carboxylates have been synthesized using two sequential carbene reactions. A dirhodium-catalyzed intramolecular cyclopropanation to form a bicyclo[1.1.0]butane is followed by a photoinduced formation of a triplet carbene, which undergoes a diradical addition into the strained C-C bond of the bicyclo[1.1.0]butane. A variety of novel 2-substituted bicyclo[1.1.1]pentanes have been synthesized in good to moderate yields, offering rapid access to these valuable scaffolds. Additionally, a one-pot, two-reaction sequence was developed in which the bicyclo[1.1.1]pentanes were afforded starting from two distinct diazo compounds. Computational analysis supports the triplet carbene intermediate addition into the bicyclo[1.1.0]butane C-C bond. Additionally, computational analysis shows the importance of an aryl substituent to stabilize the diradical intermediate, which is required for the productive formation of the bicyclo[1.1.1]pentanes.
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Registered trials
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