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Substituent-controlled, mild oxidative fluorination of iodoarenes: synthesis and structural study of aryl I(iii)- and I(v)-fluorides.
Journal article

Substituent-controlled, mild oxidative fluorination of iodoarenes: synthesis and structural study of aryl I(iii)- and I(v)-fluorides.

  • Häfliger J Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Pitts CR Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Bornemann D Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Käser R Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Santschi N Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Charpentier J Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Otth E Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Trapp N Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Verel R Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Lüthi HP Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
  • Togni A Department of Chemistry and Applied Biosciences , ETH Zürich , Vladimir-Prelog-Weg 2 , 8093 Zürich , Switzerland . Email: atogni@ethz.ch.
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  • 2019-10-08
Published in:
  • Chemical science. - 2019
General Chemistry
English We report a mild approach to the synthesis of difluoro(aryl)-λ3-iodanes (aryl-IF2 compounds) and tetrafluoro(aryl)-λ5-iodanes (aryl-IF4 compounds) using trichloroisocyanuric acid (TCICA) and potassium fluoride (KF). Under these reaction conditions, selective access to either the I(iii)- or I(v)-derivatives is predictable based solely on the substitution pattern of the iodoarene starting material. Moreover, the discovery of this TCICA/KF approach prompted detailed dynamic NMR, kinetic, computational, and crystallographic studies on the relationship between the IF2 group and the ortho-substituents on carefully designed probe molecules. It was during these experiments that the role of the ortho-substituent in inhibiting further oxidative fluorination of I(iii)-compounds to I(v)-compounds during the reaction with TCICA and KF was revealed. Additionally, a notable exception to this empirical trend is discussed herein.
Language
  • English
Open access status
gold
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Persistent URL
https://sonar.ch/global/documents/158896
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