Acid-Mediated Imidazole-to-Fluorine Exchange for the Synthesis of Sulfonyl and Sulfonimidoyl Fluorides
Marco T. Passia, Joachim Demaerel, Mostafa M. Amer, Alwin Drichel, Stefanie Zimmer, Carsten Bolm
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.
Topics & Concepts
ChemistrySulfonylFluorineImidazoleSulfurFluoridePotassium fluorideOrganic chemistryCombinatorial chemistryInorganic chemistryAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesClick Chemistry and Applications