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

doi:10.1021/acs.joc.8b01995

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

J Org Chem. 2018 Oct 5;83(19):12056-12070. doi: 10.1021/acs.joc.8b01995. Epub 2018 Sep 20.

Authors

Yulia A Vlasenko¹, Pavel S Postnikov^{1

2}, Marina E Trusova¹, Alexandr Shafir^{3

4}, Viktor V Zhdankin⁵, Akira Yoshimura^{1

5}, Mekhman S Yusubov¹

Affiliations

¹ The Tomsk Polytechnic University , 634050 Tomsk , Russia.
² University of Chemistry and Technology , 16628 Prague , Czech Republic.
³ Institute of Chemical Research of Catalonia (ICIQ) , Barcelona Institute of Science and Technology , Tarragona , Spain.
⁴ Institute of Advanced Chemistry of Catalonia (IQAC-CSIC) , Jordi Girona 18-26 , 08034 Barcelona , Spain.
⁵ Department of Chemistry and Biochemistry , University of Minnesota Duluth , Duluth , Minnesota 55812 , United States.

PMID: 30205009
DOI: 10.1021/acs.joc.8b01995

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.

Publication types

Research Support, Non-U.S. Gov't