Synthesis and Reactivity of Iodepinium Salts

Seven‐membered cyclic diaryliodonium salts, known as iodepinium salts, remain a significantly underexplored class of hypervalent iodine compounds. This scarcity is primarily attributed to the lack of efficient synthetic methodologies. Herein, we report an effective protocol for the synthesis of iodepinium triflates via the oxidative cyclization of iodinated ( Z )‐stilbenes. In addition to establishing a substrate scope of 10 derivatives with yields up to 83%, the structural features of the unique seven‐membered ring were elucidated via X‐ray crystallography. Furthermore, initial investigations into their reactivity reveal unique decomposition and transformation pathways.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-05-17
DOI
https://doi.org/10.1002/ejoc.70432
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
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article

Synthesis and Reactivity of Iodepinium Salts

Mattis Damrath, Pim Puylaert, Jan Rick Koch, Boris J. Nachtsheim
European Journal of Organic Chemistry
Oxidative Organic Chemistry Reactions
article

Synthesis and Reactivity of Iodepinium Salts

Mattis Damrath, Pim Puylaert, Jan Rick Koch, Boris J. Nachtsheim
article en

Abstract

Seven‐membered cyclic diaryliodonium salts, known as iodepinium salts, remain a significantly underexplored class of hypervalent iodine compounds. This scarcity is primarily attributed to the lack of efficient synthetic methodologies. Herein, we report an effective protocol for the synthesis of iodepinium triflates via the oxidative cyclization of iodinated ( Z )‐stilbenes. In addition to establishing a substrate scope of 10 derivatives with yields up to 83%, the structural features of the unique seven‐membered ring were elucidated via X‐ray crystallography. Furthermore, initial investigations into their reactivity reveal unique decomposition and transformation pathways.

European Journal of Organic Chemistry
University of Bremen (DE)
Openalex Percentile: Top 9%
Oxidative Organic Chemistry Reactions
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