Strategic Synthesis and Supramolecular Organization of Arylenebis(aryliodonium) Salts

Strategic Synthesis and Supramolecular Organization of Arylenebis(aryliodonium) Salts Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2025, Volume: 90, Number: 44, Pages: 15542–15554 Pages count : DOI: 10.1021/acs.joc.5c01508

Authors

Knyazeva Elizaveta V. ¹ , Soldatova Natalia S. ¹ , Abramov Pavel A. ^2,1 , Ivanov Daniil M. ^1,3 , Burykina Julia V. ⁴ , Radzhabov Amirbek D. ¹ , Yusubov Mekhman S. ¹ , Resnati Giuseppe ^5,1 , Kukushkin Vadim Yu. ² , Postnikov Pavel S. ^1,6

Affiliations

1	Tomsk Polytechnic University, Tomsk 634034, Russian Federation
2	Nikolaev Institute of Inorganic Chemistry SB RAS, 3 acad. Lavrentiev Ave., 630090 Novosibirsk, Russian Federation
3	Nikolaev Institute of Inorganic Chemistry SB RAS, 3 acad. Lavrentiev Ave., 630090 Novosibirsk, Russian Federation
4	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, Moscow, 119991, Russian Federation
5	Politecnico di Milano, Department of Chemistry, Materials, Chemical Engineer., via Mancinelli 7, 20131 Milan, Italy
6	N.N. Vorozhtsov Institute of Organic Chemistry, Pr. Ak. Lavrentieva 9, Novosibirsk 630090, Russian Federation

A comprehensive synthetic toolkit was developed for the preparation of arylenebis(aryliodonium) salts from diiodoarenes via m-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.

Knyazeva E.V. , Soldatova N.S. , Abramov P.A. , Ivanov D.M. , Burykina J.V. , Radzhabov A.D. , Yusubov M.S. , Resnati G. , Kukushkin V.Y. , Postnikov P.S.
Strategic Synthesis and Supramolecular Organization of Arylenebis(aryliodonium) Salts
Journal of Organic Chemistry. 2025. V.90. N44. P.15542–15554. DOI: 10.1021/acs.joc.5c01508 WOS Scopus OpenAlex

≡ Web of science:	WOS:001604948700001
≡ Scopus:	2-s2.0-105021041246
≡ OpenAlex:	W4415685132