College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong, 266109, China.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191, China.
Angew Chem Int Ed Engl. 2023 Mar 1;62(10):e202215008. doi: 10.1002/anie.202215008. Epub 2023 Jan 12.
Trifluoromethanesulfonic anhydride has been widely used in synthetic organic chemistry, not only for the conversion of various oxygen-containing compounds to the triflates, but also for the electrophilic activation and further conversion of amides, sulfoxides, and phosphorus oxides. In recent years, the utilization of Tf O as an activator for nitrogen-containing heterocycles, nitriles and nitro groups has become a promising tool for the development of new valuable methods with considerable success. In addition, Tf O has been used as an efficient radical trifluoromethylation and trifluoromethylthiolation reagent due to the contained SO CF fragment, and significant progress has been made in this area. This review summarizes the recent progress in the applications of Tf O in the above two aspects, and aims to illustrate the role and potential application of this reagent in organic synthesis.
三氟甲磺酸酐在有机合成中得到了广泛的应用,不仅可以将各种含氧化合物转化为三氟甲磺酸酯,还可以对酰胺、亚砜和磷氧化物进行亲电活化和进一步转化。近年来,TfO 作为含氮杂环、腈和硝基的活化剂,已经成为开发具有相当成功的新有价值方法的有前途的工具。此外,由于含有 SOCF 片段,TfO 还可用作有效的自由基三氟甲基化和三氟甲硫基化试剂,在这方面取得了重大进展。本综述总结了 TfO 在上述两个方面的应用的最新进展,旨在说明该试剂在有机合成中的作用和潜在应用。