Organic Letters
Author:
Keywords:
Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, NUCLEOPHILIC-SUBSTITUTION, EFFICIENT SYNTHESIS, LEAVING-GROUP, SULFUR, AMINOLYSIS, REAGENTS, SUFEX, 12ZL820N#55266849, 03 Chemical Sciences, Organic Chemistry, 34 Chemical sciences
Abstract:
Sulfur(VI) fluoride motifs are important entities in organic chemistry. Typically, their syntheses involve the corresponding chlorides, which are often difficult to prepare and characterized by a poor storability due to the inherently weak S−Cl bond. Here, a single-step procedure for the preparation of sulfur(VI) fluorides starting from sulfonyl imidazoles as stable S(VI) reservoirs is described. By using a simple combination of AcOH and potassium bifluoride (KF2H), an imidazole-to-fluorine exchange furnishes a variety of sulfonyl, sulfonimidoyl, sulfoxyl, and sulfamoyl fluorides in good to excellent yields.