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 › peer-review

11 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

ASJC Scopus subject areas

Organic Chemistry

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Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts. / Vlasenko, Yulia A.; Postnikov, Pavel S.; Trusova, Marina E.; Shafir, Alexandr; Zhdankin, Viktor V.; Yoshimura, Akira ; Yusubov, Mekhman S.

In: Journal of Organic Chemistry, Vol. 83, No. 19, 05.10.2018, p. 12056-12070.

Research output: Contribution to journal › Article › peer-review

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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.",

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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

N2 - 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.

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

Abstract

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