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

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

doi:10.1021/acs.joc.8b01995

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

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

Chemistry & Biochemistry

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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 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 (US)
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
State	Published - Oct 5 2018

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© 2018 American Chemical Society.

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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.",

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doi = "10.1021/acs.joc.8b01995",

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AU - Vlasenko, Yulia A.

AU - Postnikov, Pavel S.

AU - Trusova, Marina E.

AU - Shafir, Alexandr

AU - Zhdankin, Viktor

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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