Cu-Catalyzed SF4-Alkynylation of Quinolones, Chromones and Cyclohexenones

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-10 DOI:10.1021/acs.orglett.5c03631

Muhamad Zulfaqar Bacho, Yuji Sumii, Ankit Kumar, Shiwei Wu, Norio Shibata

引用次数: 0

Abstract

We report the Cu-catalyzed SF₄-alkynylation of quinolones, chromones, and cyclohexenones using pyridyl SF₄-alkynes under Lewis acid assisted conditions, affording diverse SF₄-linked heterocycles in good to high yields. The method leverages the electron-deficient, enone-like character of SF₄-alkynes while maintaining broad functional group tolerance. Notably, the SF₄ unit remains stable under oxidative and acidic conditions, enabling efficient ring-reconstruction from six- to five-membered heterocycles. This strategy provides access to regulation-friendly fluorinated scaffolds with significant potential in medicinal chemistry.

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铜催化喹诺酮类、铬酮类和环己酮类的sf4炔化反应

我们报道了在Lewis酸辅助条件下，以吡啶sf4 -炔为原料，cu催化喹诺酮类、铬酮类和环己酮类化合物的sf4 -炔化反应，得到了多种sf4连接的杂环化合物，收率高。该方法利用sf4 -炔的缺电子、类烯酮的特性，同时保持广泛的官能团耐受性。值得注意的是，SF4单元在氧化和酸性条件下保持稳定，能够从六元到五元杂环进行有效的环重建。这一策略提供了在药物化学中具有巨大潜力的监管友好的氟化支架。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.