ReviewBeilstein journal of organic chemistry2023
Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control.
Review in Beilstein journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 17 citations in OpenAlex.
- Solid-to-Solid Zn Anode and Interhalogen Iodine Cathodes for High-Voltage Fluoride-Ion Batteries.Angewandte Chemie (International ed. in English) · 2026Article
- Photocatalytic Activation of Heterocyclic Iodonium Ylides for the Synthesis of Dihydrofuropyranones and Dihydrofuropyridones.The Journal of organic chemistry · 2025Article
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- A decade of lessons in the activation of ArILChemical science · 2024Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
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Abstract
Halogen bonding is commonly found with iodine-containing molecules, and it arises when Lewis bases interact with iodine's σ-holes. Halogen bonding and σ-holes have been encountered in numerous monovalent and hypervalent iodine-containing compounds, and in 2022 σ-holes were computationally confirmed and quantified in the iodonium ylide subset of hypervalent iodine compounds. In light of this new discovery, this article provides an overview of the reactions of iodonium ylides in which halogen bonding has been invoked. Herein, we summarize key discoveries and mechanistic proposals from the early iodonium ylide literature that invoked halogen bonding-type mechanisms, as well as recent reports of reactions between iodonium ylides and Lewis basic nucleophiles in which halogen bonding has been specifically invoked. The reactions discussed herein are organized to enable the reader to build an understanding of how halogen bonding might impact yield and chemoselectivity outcomes in reactions of iodonium ylides. Areas of focus include nucleophile σ-hole selectivity, and how ylide structural modifications and intramolecular halogen bonding (e.g., the
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