Houston Sevan D, Sharp-Bucknall Lachlan, Poynder Tiffany B, Albayer Mohammad, Dutton Jason L
Department of Chemistry and Physics, La Trobe University, Melbourne, Victoria, Australia.
Chemistry. 2020 Dec 4;26(68):15863-15866. doi: 10.1002/chem.202003819. Epub 2020 Oct 29.
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.
在过去30年中,二醋酸碘苯(PhI(OTf))一直被用作一种强三价碘(I(III))氧化剂,用于有机和无机转化反应。据报道,它可由二醋酸碘苯(PhI(OAc))或二氧碘苯(PhI=O)与两当量的三甲基甲硅烷基三氟甲磺酸酯(TMS-OTf)反应原位生成。本报告表明,这些反应均未生成具有与二醋酸碘苯(PhI(OTf))相符的光谱数据的溶液,理论计算也提供了支持,因此,在那些与使用该化合物相关的转化反应中,不应将其作为起氧化剂作用的物种。