Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.
Molecules. 2022 Aug 15;27(16):5201. doi: 10.3390/molecules27165201.
Among the variety of sulfonamides, triflamides (CFSONHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties. Their strong electron-withdrawing properties and low nucleophilicity, combined with their high NH-acidity, makes it possible to use triflamides in a vast variety of organic reactions. This review is devoted to the synthesis and use of -trifluoromethanesulfonyl derivatives in organic chemistry, medicine, biochemistry, catalysis and agriculture. Part of the work is a review of areas and examples of the use of bis(trifluoromethanesulfonyl)imide (triflimide, (CFSO)NH, TfNH). Being one of the strongest NH-acids, triflimide, and especially its salts, are widely used as catalysts in cycloaddition reactions, Friedel-Crafts reactions, condensation reactions, heterocyclization and many others. Triflamides act as a source of nitrogen in C-amination (sulfonamidation) reactions, the products of which are useful building blocks in organic synthesis, catalysts and ligands in metal complex catalysis, and have found applications in medicine. The addition reactions of triflamide in the presence of oxidizing agents to alkenes and dienes are considered separately.
在各种磺胺类化合物中，三氟甲磺酰胺（CFSONHR，TfNHR）在有机化学中占据特殊地位。三氟甲磺酰胺广泛用作试剂，在许多反应中是高效的催化剂或添加剂。这些化合物被广泛应用的原因是它们具有高 NH 酸度、亲脂性、催化活性和特定的化学性质。其强吸电子性质和低亲核性，与高 NH 酸度相结合，使得三氟甲磺酰胺能够用于各种有机反应中。本综述致力于讨论 -三氟甲磺酰基衍生物在有机化学、医学、生物化学、催化和农业中的合成和应用。部分工作是对双（三氟甲磺酰基）亚胺（三氟甲磺酰亚胺，（CFSO）NH，TfNH）的用途和应用领域进行综述。作为最强的 NH 酸之一，三氟甲磺酰亚胺及其盐广泛用作环加成反应、傅克反应、缩合反应、杂环化和许多其他反应的催化剂。三氟甲磺酰胺作为 C-胺化（磺酰胺化）反应中的氮源，其产物是有机合成中的有用构建块、金属配合物催化中的催化剂和配体，并在医学中得到应用。还分别考虑了在氧化剂存在下三氟甲磺酰胺与烯烃和二烯的加成反应。
