Synthesis of arylbenziodoxoles using pseudocyclic benziodoxole triflate and arenes

Akira Yoshimura, Scott M. Larson, Gunnar B. Frahm, Christopher D. Huss, Gregory T. Rohde, Victor N. Nemykin, Mekhman S. Yusubov, Akio Saito, Viktor V. Zhdankin

Research output: Contribution to journalArticlepeer-review

Abstract

An acid activated pseudocyclic hypervalent iodine reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]-iodobenzoic acid, can easily react with various arenes in the presence of trifluoromethanesulfonic acid to produce pseudocyclic diaryliodonium triflate salts. This synthetic procedure proceeds under mild conditions to afford the respective iodonium salts in moderate to good yields. Several pseudocyclic diaryliodonium triflate salts structures have been confirmed by X-ray crystallography. Obtained products can be easily converted to cyclic hypervalent iodine(III) compounds, arylbenziodoxolones, in moderate to good yields under basic conditions.

Original languageEnglish (US)
JournalArkivoc
Volume2020
Issue number4
DOIs
StatePublished - Sep 24 2020

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P) and National Science Foundation (CHE-1759798). A.S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2).

Keywords

  • Arylbenziodoxolones
  • Benziodoxole
  • Cyclization
  • Hypervalent iodine reagent
  • Pseudocyclic diaryliodonium salts

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