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 journalArticle

8 Citations (Scopus)

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
Pages (from-to)16738-16742
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number66
DOIs
Publication statusPublished - 27 Nov 2017

Fingerprint

Iodine compounds
Iodine Compounds
X ray crystallography
Phenol
Iodine
Phenols
Salts
Single crystals
Oxygen
Acids
Water
Substrates
Temperature
benzyne
trifluoromethanesulfonic acid

Keywords

  • arynes
  • benzyne
  • hypervalent iodine
  • iodine
  • iodonium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Pseudocyclic Arylbenziodoxaboroles : Efficient Benzyne Precursors Triggered by Water at Room Temperature. / Yoshimura, Akira; Fuchs, Jonathan M.; Middleton, Kyle R.; Maskaev, Andrey V.; Rohde, Gregory T.; Saito, Akio; Postnikov, Pavel S.; Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.

In: Chemistry - A European Journal, Vol. 23, No. 66, 27.11.2017, p. 16738-16742.

Research output: Contribution to journalArticle

Yoshimura, Akira ; Fuchs, Jonathan M. ; Middleton, Kyle R. ; Maskaev, Andrey V. ; Rohde, Gregory T. ; Saito, Akio ; Postnikov, Pavel S. ; Yusubov, Mekhman S. ; Nemykin, Victor N. ; Zhdankin, Viktor V. / Pseudocyclic Arylbenziodoxaboroles : Efficient Benzyne Precursors Triggered by Water at Room Temperature. In: Chemistry - A European Journal. 2017 ; Vol. 23, No. 66. pp. 16738-16742.
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