Strategic Synthesis and Supramolecular Organization of Arylenebis(aryliodonium) Salts
A comprehensive synthetic toolkit was developed for the preparation of arylenebis(aryliodonium) salts from diiodoarenes via <i>m</i>-CPBA oxidation. The methodology offers versatile approaches that can be adapted based on the solubility of reaction intermediates, enabling either one-pot or two-stage synthesis pathways. Four distinct synthetic methods were established, accommodating a wide range of arenes and diiodoarenes, including sterically hindered and electron-deficient substrates. The resulting bis(iodonium) salts were isolated in good to excellent yields (up to 99%). X-ray crystallographic analysis of these compounds revealed intriguing supramolecular organization in the solid state, with the formation of 1D chains through halogen bonding interactions. These self-assembled architectures demonstrate the potential of bis(iodonium) cations as valuable building blocks for applications in crystal engineering.
Authors
- Giuseppe Resnati (ORCID: https://orcid.org/0000-0002-0797-9296)
- Natalia S. Soldatova (ORCID: https://orcid.org/0000-0002-1738-4747)
- Amirbek D. Radzhabov (ORCID: https://orcid.org/0000-0001-8138-6344)
- Julia V. Burykina (ORCID: https://orcid.org/0000-0001-6286-1699)
- Vadim Yu. Kukushkin (ORCID: https://orcid.org/0000-0002-2253-085X)
- Daniil M. Ivanov (ORCID: https://orcid.org/0000-0002-0855-2251)
- Mekhman S. Yusubov (ORCID: https://orcid.org/0000-0001-9233-1824)
- Павел Сергеевич Постников (ORCID: https://orcid.org/0000-0001-9713-1290)
- Pavel A. Abramov⧫ (ORCID: https://orcid.org/0000-0003-4479-5100)
- E. Knyazeva (ORCID: https://orcid.org/0000-0003-2427-0884)
Institutions
- St Petersburg University (RU)
- National Research Tomsk State University (RU)
- Tomsk Polytechnic University (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
- Novosibirsk Institute of Organic Chemistry (RU)
- Nikolaev Institute of Inorganic Chemistry (RU)
- Politecnico di Milano (IT)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-30
- DOI
- https://doi.org/10.1021/acs.joc.5c01508
- Citations
- 1
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94