Acid-Mediated Imidazole-to-Fluorine Exchange for the Synthesis of Sulfonyl and Sulfonimidoyl Fluorides

Passia, Marco T; Demaerel, Joachim; Amer, Mostafa M; Drichel, Alwin; Zimmer, Stefanie; Bolm, Carsten

doi:10.1021/acs.orglett.2c03546

Acid-Mediated Imidazole-to-Fluorine Exchange for the Synthesis of Sulfonyl and Sulfonimidoyl Fluorides

Author:

Passia, Marco T

Demaerel, Joachim ; Amer, Mostafa M ; Drichel, Alwin ; Zimmer, Stefanie ; Bolm, Carsten

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.