ArticleAngewandte Chemie (International ed. in English)2025
Synthesis of Bicyclo[1.1.1]Pentane Z-Substituted Enamides, Enol Ethers, and Vinyl Sulfides Using Iodine (III) Reagents.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Hypervalent iodine reagents in organic synthesis: a review of methodology developments and synthetic applications.RSC advances · 2026Review
- Peptide/Protein Functionalization and Macrocyclization via Alkyne Umpolung with Hypervalent Iodine Reagents.Accounts of chemical research · 2025Article
- Synthesis of Bicyclo[1.1.1]Pentane Z-Substituted Enamides, Enol Ethers, and Vinyl Sulfides Using Iodine (III) Reagents.Angewandte Chemie (International ed. in English) · 2025Article
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4 authors.
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Abstract
Bicyclo[1.1.1]pentanes (BCPs) are well-studied bioisosteres for para-substituted benzene rings, and numerous methods for synthesizing 1,3-difunctionalized BCPs have been developed. However, synthetic approaches to access vinyl BCP motifs remain limited, with only few reports on the synthesis of BCP-olefins bearing heteroatom substituents. Herein, we present the synthesis of BCP-substituted enamides, enol ethers, and vinyl sulfides through the sequential functionalization of ethynylbenziodoxolone (EBX) reagents containing a BCP scaffold. Stereoselective addition of a nucleophile generates heteroatomic Z-vinylbenziodoxolone (VBX) reagents. The hypervalent iodine substituent of the VBX reagents serves then as a versatile platform for further arylation, vinylation, and trifluoromethylation. This method provides a modular synthesis of previously inaccessible heteroatom-substituted vinyl BCPs.
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