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PhI(OTf)2 Does Not Exist (Yet)*.

Tania1, Sevan D Houston1, Lachlan Sharp-Bucknall1

  • 1Department of Chemistry and Physics, La Trobe University, Melbourne, Victoria, Australia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
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PubMed
Summary
This summary is machine-generated.

Phenyliodine(III) bis(trifluoromethanesulfonate) [PhI(OTf)2] is a commonly used oxidant. However, this study demonstrates that common methods do not actually produce PhI(OTf)2, challenging its role in many reactions.

Keywords:
NMR spectroscopyhypervalentintermediatesiodineoxidants

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Area of Science:

  • Organic Chemistry
  • Hypervalent Iodine Chemistry

Background:

  • Phenyliodine(III) bis(trifluoromethanesulfonate) [PhI(OTf)2] has been widely utilized as a potent hypervalent iodine(III) oxidant in organic and inorganic synthesis for three decades.
  • It is traditionally believed to be generated in situ via reactions involving phenyliodine(III) diacetate [PhI(OAc)2] or phenyliodine(III) oxide [PhI=O] with trimethylsilyl trifluoromethanesulfonate (TMS-OTf).

Purpose of the Study:

  • To rigorously investigate the actual species formed under conditions previously attributed to PhI(OTf)2.
  • To re-evaluate the mechanistic role of PhI(OTf)2 in established synthetic transformations.

Main Methods:

  • Spectroscopic analysis (e.g., NMR, IR) of reaction mixtures generated under purported PhI(OTf)2 formation conditions.
  • Computational chemistry calculations to support experimental observations and predict species stability.

Main Results:

  • Spectroscopic data obtained from the in situ generation methods are inconsistent with the presence of PhI(OTf)2.
  • Theoretical calculations corroborate the experimental findings, indicating that PhI(OTf)2 is not the actual species formed.

Conclusions:

  • The commonly employed methods for generating PhI(OTf)2 in situ do not yield this specific hypervalent iodine(III) compound.
  • The oxidizing capabilities previously ascribed to PhI(OTf)2 likely originate from other reactive species present in the reaction mixtures.
  • Revisiting the mechanisms of reactions involving these generation methods is necessary.