Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature

Akira Yoshimura, Jonathan M. Fuchs, Kyle R. Middleton, Andrey V. Maskaev, Gregory T. Rohde, Akio Saito, Pavel S. Postnikov, Mekhman S. Yusubov, Victor N. Nemykin, Viktor V. Zhdankin

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

New organohypervalent iodine compounds, arylbenziodoxaborole triflates, were prepared from 1-acetoxybenziodoxaboroles and arenes by treatment with trifluoromethanesulfonic acid under mild conditions. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.698 to 2.717 Å between oxygen and iodine in the benziodoxaborole ring. These new pseudocyclic aryliodonium salts readily generate aryne intermediates upon treatment with water at room temperature. The generated aryne intermediates react with various substrates to give the corresponding aryne adducts in moderate to good yields. Furthermore, the new benzyne precursors can also work as arylating reagents towards aromatic rings. The aryne intermediates generated from arylbenziodoxaborole triflates selectively react with tert-butyl phenol forming products of ortho arylation in moderate yields.

Original languageEnglish (US)
Pages (from-to)16738-16742
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number66
DOIs
StatePublished - Nov 27 2017

Bibliographical note

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479), the Russian Science Foun- dation (RSF-16-13-10081), and Tomsk Polytechnic University (VIU-316/2017). A.S. is also thankful to JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15K07852).

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479), the Russian Science Foundation (RSF-16-13-10081), and Tomsk Polytechnic University (VIU-316/2017). A.S. is also thankful to JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15K07852).

Keywords

  • arynes
  • benzyne
  • hypervalent iodine
  • iodine
  • iodonium

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