ArticleJournal of the American Chemical Society2025
A Unified Synthetic Approach to 2-Alkyl Azetidines, Oxetanes, Thietanes and Cyclobutanes from Unactivated Alkenes.
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 4 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
4 citing papers in PubMed.
- Oxetane-to-azetidine skeletal editing.Nature chemistry · 2026Article
- Deoxygenative Single-Carbon Atom Transfer: Accessing Strained Carbocycles From Alkenes and Aldehydes With Designer Dual-Functional Reagent.Angewandte Chemie (International ed. in English) · 2026Article
- A 10-Year Journey Into Diverse Arylsulfonium Salts: Versatile Reagents for Organic Synthesis.Chemical record (New York, N.Y.) · 2026Article
- The Synthesis of Tertiary Alkylamines from Alkyl-Substituted Alkenes Using Amine Umpolung Strategy.Journal of the American Chemical Society · 2026Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
2-Alkyl substituted four-membered carbocycles and heterocycles are relevant motifs in pharmaceuticals and agrochemicals. However, synthetic methods to access these scaffolds mostly rely on functional group interconversion of a narrow subset of preformed cyclic building blocks, impeding access to a broad chemical space. In this report, we introduce a general method to transform readily available unactivated alkenes into 2-alkyl four-membered rings. In contrast to classic [2 + 2] cycloaddition chemistry─which is not viable for this class of products─our strategy leverages a homologative alkene dielectrophilic activation, converting the starting alkene into a transient 1,3-iodo-sulfonium intermediate, which undergoes sequential nucleophilic substitutions to promote ring formation. The chemical versatility of the intermediate enables modulation of the order of substitutions, crucial to targeting the full matrix of four-membered rings─i.e., azetidines, oxetanes, thietanes, and cyclobutanes. This functional group tolerant process is applicable to a wide range of alkenes─including complex structures─opening new avenues for applications in pharmaceutical and agrochemical synthesis.
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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.