Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts

Yulia A. Vlasenko, Pavel S. Postnikov, Marina E. Trusova, Alexandr Shafir, Viktor V. Zhdankin, Akira Yoshimura, Mekhman S. Yusubov

Research School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article

7 Citations (Scopus)

Abstract

Pseudocyclic 2-benzimidazolyl-substituted diaryliodonium salts were obtained by the reaction of the corresponding [hydroxy(tosyloxy)iodo]arenes with arenes in the presence of trifluoromethanesulfonic acid. X-ray structural analysis of these iodonium salts confirmed their pseudocyclic structure with a short (2.57-2.58 Å) noncovalent I···N interaction. Treatment of 2-benzimidazolyl-substituted diaryliodonium triflates with a base afforded novel five-membered iodine-nitrogen heterocycles.

Original language	English
Pages (from-to)	12056-12070
Number of pages	15
Journal	Journal of Organic Chemistry
Volume	83
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.8b01995
Publication status	Published - 5 Oct 2018

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Vlasenko, Y. A., Postnikov, P. S., Trusova, M. E., Shafir, A., Zhdankin, V. V., Yoshimura, A., & Yusubov, M. S. (2018). Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts. Journal of Organic Chemistry, 83(19), 12056-12070. https://doi.org/10.1021/acs.joc.8b01995

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title = "Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts",

abstract = "Pseudocyclic 2-benzimidazolyl-substituted diaryliodonium salts were obtained by the reaction of the corresponding [hydroxy(tosyloxy)iodo]arenes with arenes in the presence of trifluoromethanesulfonic acid. X-ray structural analysis of these iodonium salts confirmed their pseudocyclic structure with a short (2.57-2.58 {\AA}) noncovalent I···N interaction. Treatment of 2-benzimidazolyl-substituted diaryliodonium triflates with a base afforded novel five-membered iodine-nitrogen heterocycles.",

author = "Vlasenko, {Yulia A.} and Postnikov, {Pavel S.} and Trusova, {Marina E.} and Alexandr Shafir and Zhdankin, {Viktor V.} and Akira Yoshimura and Yusubov, {Mekhman S.}",

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T1 - Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts

AU - Vlasenko, Yulia A.

AU - Postnikov, Pavel S.

AU - Trusova, Marina E.

AU - Shafir, Alexandr

AU - Zhdankin, Viktor V.

AU - Yoshimura, Akira

AU - Yusubov, Mekhman S.

PY - 2018/10/5

Y1 - 2018/10/5

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AB - Pseudocyclic 2-benzimidazolyl-substituted diaryliodonium salts were obtained by the reaction of the corresponding [hydroxy(tosyloxy)iodo]arenes with arenes in the presence of trifluoromethanesulfonic acid. X-ray structural analysis of these iodonium salts confirmed their pseudocyclic structure with a short (2.57-2.58 Å) noncovalent I···N interaction. Treatment of 2-benzimidazolyl-substituted diaryliodonium triflates with a base afforded novel five-membered iodine-nitrogen heterocycles.

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Access to Document

10.1021/acs.joc.8b01995