PhI(OTf)2 Does Not Exist (Yet)

Tania,; Houston, Sevan; Sharp-Bucknall, Lachlan; Poynder, Tiffany; Al Bayer, Mohammad; Dutton, Jason

doi:10.26181/607fd08035861

PhI(OTf)2_suppinfo_revise_final.docx (2.11 MB)

PhI(OTf)2 Does Not Exist (Yet)

journal contribution

posted on 21.04.2021, 06:49 authored by Tania, Sevan Houston, Lachlan Sharp-BucknallLachlan Sharp-Bucknall, Tiffany Poynder, Mohammad Al BayerMohammad Al Bayer, Jason DuttonJason Dutton

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.

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.

History

Publication Date

04/12/2020

Journal

Chemistry: A European Journal

Volume

26

Issue

68

Pagination

4p. (p. 15863-15866)

Publisher

Wiley

ISSN

0947-6539

Rights Statement

The Author reserves all moral rights over the deposited text and must be credited if any re-use occurs. Documents deposited in OPAL are the Open Access versions of outputs published elsewhere. Changes resulting from the publishing process may therefore not be reflected in this document. The final published version may be obtained via the publisher’s DOI. Please note that additional copyright and access restrictions may apply to the published version.