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Updated: Feb 28, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of γ-Carbonyl Aliphatic Sulfoxonium Salts via Site-Selective Ring Opening of In Situ Formed 2-Sulfoxonium
Bingyang Han1, Zihui Gong1, Zhaofeng Wang1
1State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, People's Republic of China.
Abstract:
We report herein a Rh-catalyzed tandem reaction between a pivaloyl-substituted sulfoxonium-iodonium ylide and diverse nucleophiles, enabling the efficient synthesis of γ-sulfoxonium carbonyl compounds, which were previously inaccessible. This transformation proceeds through a novel site-selective ring-opening of in situ-generated 2-sulfoxonium cyclobutanone by N-, O-, S-, and Se-centered nucleophiles. The reaction exhibits mild conditions, a broad substrate scope, and excellent scalability. Additionally, the resulting γ-sulfoxonium amides can undergo base-promoted intramolecular cyclization to afford γ-lactams, which are valuable scaffolds in medicinal chemistry.
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