ArticleJournal of the American Chemical Society2024
Stereoselective Alder-Ene Reactions of Bicyclo[1.1.0]butanes: Facile Synthesis of Cyclopropyl- and Aryl-Substituted Cyclobutenes.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Visible light-mediated Alder-ene reaction of bicyclobutanes with cyclohexynes to access skipped dienes and skeletal remodeling to tetralines.Nature communications · 2026Article
- Concise synthesis and strain-release diversification of bridgehead-substituted [2]-ladderanes.Nature chemistry · 2026Article
- Recent Progress in Coupling Reactions Involving the Novel Substrate of Bicyclo[1.1.0]butane (BCB).Topics in current chemistry (Cham) · 2026Review
- Ring expansion of bicyclo[1.1.0]butyl ketones to bicyclo[2.1.1]hexenes using ketone as both activating and reacting groups.Nature communications · 2025Article
- Photoinduced cobaloxime catalysis enabled dehydrogenative C2-phosphinylation of bicyclo[1.1.0]butanes to access phosphorylated cyclobutenes.RSC advances · 2025Article
- Catalyst-Controlled Divergent Synthesis of Bicyclo[2.1.1]hexanes and Cyclobutenes: The Unique Effect of Au(I).JACS Au · 2025Article
- Generation and Use of Bicyclo[1.1.0]butyllithium under Continuous Flow Conditions.Organic letters · 2025Article
- Article
- Strain-release trifluoromethoxylation and pentafluorosulfanoxylation of [1.1.0]bicyclobutanes: expanded access to fluorinated cyclobutane hybrid bioisosteres.Chemical communications (Cambridge, England) · 2025Article
- Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C-C cleavage and ruthenium-catalysed remote C-H activation.Nature synthesis · 2025Article
- Ligand-controlled regiodivergent aminocarbonylation of cyclobutanols toward 1,1- and 1,2-substituted cyclobutanecarboxamides.Nature communications · 2024Article
- Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes.Chemical science · 2024Article
- Synthesis of Stereodefined Polysubstituted Bicyclo[1.1.0]butanes.Journal of the American Chemical Society · 2024Article
- Umpolung reactivity of strained C-C σ-bonds without transition-metal catalysis.Nature communications · 2024Article
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Authors and funding
8 authors.
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No grant is acknowledged in the PubMed record.
Abstract
Bicyclo[1.1.0]butanes (BCBs), strained carbocycles comprising two fused cyclopropane rings, have become well-established building blocks in organic synthesis, medicinal chemistry, and chemical biology due to their diverse reactivity profile with radicals, nucleophiles, cations, and carbenes. The constraints of the bicyclic ring system confer high p-character on the interbridgehead C-C bond, leading to this broad reaction profile; however, the use of BCBs in pericyclic processes has to date been largely overlooked in favor of such stepwise, non-concerted additions. Here, we describe the use of BCBs as substrates for ene-like reactions with strained alkenes and alkynes, which give rise to cyclobutenes decorated with highly substituted cyclopropanes and arenes. The former products are obtained from highly stereoselective reactions with cyclopropenes, generated in situ from vinyl diazoacetates under blue light irradiation (440 nm). Cyclobutenes featuring a quaternary aryl-bearing carbon atom are prepared from equivalent reactions with arynes, which proceed in high yields under mild conditions. Mechanistic studies highlight the importance of electronic effects in this chemistry, while computational investigations support a concerted pathway and rationalize the excellent stereoselectivity of reactions with cyclopropenes.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.