Ruthenium Catalyzed Mechanochemical Transformation of Sulfonamide Group to Fluoro, Trifluoromethyl, and Trifluoromethoxy Functionalities

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-04-09 DOI:10.1002/asia.202500221

Satenik Mkrtchyan, Vishal B. Purohit, Vaibhav D. Prajapati, Ronak V. Prajapati, Oleksandr Shalimov, Sehrish Sarfaraz, Khurshid Ayub, Viktor O. Iaroshenko

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引用次数: 0

Abstract

A convenient route for the mechanochemical synthesis of fluorinated aromatic compounds, that is, fluoro, trifluoromethyl, and trifluoromethoxy arenes, has been developed via pyrylium tetrafluoroborate (Pyry-BF₄)-mediated desulfonamidative cross-coupling of primary sulfonamides under the synergy of a piezoelectric material BaTiO₃, and Ru-catalysis. This is the first-ever report on the selective transformation of sulfonamide (SO₂NH₂) functionality to CF₃/OCF₃/F group in a single step under mechanochemical ball-milling conditions. Considering the importance of primary sulfonamides as the valuable pharmacophores, the present desulfonamidative cross-coupling approach could have potential to get synthetic utility in pharmaceutical industries for the late-stage functionalization of sulfonamide drugs and related active pharmaceutical ingredients (APIs).

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钌催化磺胺基向氟、三氟甲基和三氟甲氧基官能团的机械化学转化。

在压电材料BaTiO3和ru的协同作用下，通过四氟硼酸吡啶（Pyry-BF4）介导的伯胺类磺胺的脱硫酰胺交叉偶联，开发了一种方便的机械化学合成含氟芳香化合物氟、三氟甲基和三氟甲氧基芳烃的途径。这是首次报道在机械化学球磨条件下，单步选择性地将磺胺（SO2NH2）功能转化为CF3/OCF3/F基团。考虑到原胺类药物作为一种有价值的药效载体的重要性，本文提出的脱硫酰胺交叉偶联方法在磺胺类药物及相关活性药物成分的后期功能化方面具有潜在的合成应用前景。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).