Acid-mediated imidazole-to-fluorine exchange for the synthesis of sulfonyl and sulfonimidoyl fluorides

MT Passia, J Demaerel, MM Amer, A Drichel… - Organic …, 2022 - ACS Publications
MT Passia, J Demaerel, MM Amer, A Drichel, S Zimmer, C Bolm
Organic Letters, 2022ACS Publications
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 …
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.
ACS Publications
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