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

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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 languageEnglish
Pages (from-to)12056-12070
Number of pages15
JournalJournal of Organic Chemistry
Volume83
Issue number19
DOIs
Publication statusPublished - 5 Oct 2018

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Iodine
Nitrogen
Salts
Structural analysis
X rays
benzimidazole
trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.}",
year = "2018",
month = "10",
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doi = "10.1021/acs.joc.8b01995",
language = "English",
volume = "83",
pages = "12056--12070",
journal = "Journal of Organic Chemistry",
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publisher = "American Chemical Society",
number = "19",

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TY - JOUR

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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