PhI(OTf) has been used for the past 30 years as a strong I(III) oxidant for organic and inorganic transformations. It has been reported to be generated in situ from the reactions of either PhI(OAc) or PhI=O with two equivalents of trimethylsilyl trifluoromethanesulfonate (TMS-OTf). In this report it is shown that neither of these reactions generate a solution with spectroscopic data consistent with PhI(OTf) , with supporting theoretical calculations, and thus this compound should not be invoked as the species acting as the oxidant for transformations that have been associated with its use.<p></p>
Funding
We thank La Trobe University and the Australian Research Council (FT16010007, DP200100013) for their generous funding of this work. We thank Dr. Christian Hering-Junghans for providing a 1HNMR of TMS-OAc in CD3CN.
Publication Date
2020-12-04Journal
Chemistry: A European JournalVolume
26Issue
68Pagination
4p. (p. 15863-15866)Publisher
WileyISSN
0947-6539Rights Statement
© 2020 Wiley-VCH GmbH. This is the peer reviewed version of the following article: Tania T, et al (2020). PhI(OTf)2 Does Not Exist (Yet). Chemistry - A European Journal, 26(68), 15863-15866, which has been published in final form at http://doi.org/10.1002/chem.202003819. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
