PhI(OTf)2 Does Not Exist (Yet)

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

doi:10.26181/14451294.v2

PhI(OTf)2 Does Not Exist (Yet)

Version 2 2023-12-19, 03:08

Version 1 2021-04-21, 06:49

journal contribution

posted on 2023-12-19, 03:08 authored by Tania TaniaTania Tania, Sevan Houston, Lachlan 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

2020-12-04

Journal

Chemistry: A European Journal

Volume

26

Issue

68

Pagination

4p. (p. 15863-15866)

Publisher

Wiley

ISSN

0947-6539

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