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Acid-Mediated Imidazole-to-Fluorine Exchange for the Synthesis of Sulfonyl and Sulfonimidoyl Fluorides
Organic Letters ( IF 4.9 ) Pub Date : 2022-11-23 , DOI: 10.1021/acs.orglett.2c03546
Marco T Passia 1 , Joachim Demaerel 1, 2 , Mostafa M Amer 1, 3 , Alwin Drichel 1 , Stefanie Zimmer 1 , Carsten Bolm 1
Affiliation  

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.

中文翻译:

酸介导的咪唑-氟交换合成磺酰基和磺酰亚胺酰氟

硫 (VI) 氟化物基序是有机化学中的重要实体。通常,它们的合成涉及相应的氯化物,这些氯化物通常难以制备,并且由于固有的弱 S-Cl 键而具有较差的储存性。在这里,描述了从磺酰咪唑作为稳定的 S(VI)储层开始制备硫(VI)氟化物的单步程序。通过使用 AcOH 和氟化氢钾 (KF 2 H) 的简单组合,咪唑到氟的交换可提供各种磺酰基、亚磺酰亚胺酰基、亚磺酰基和氨磺酰氟,产率从高到高。
更新日期:2022-11-23
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