Palladium-Catalyzed Decarboxylative Cross-Couplings of Zinc Polyfluorobenzoates with Aryl 2-Pyridyl Esters for Accessing Polyfluorinated Aryl Ketones.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-27 DOI:10.1021/acs.orglett.5c01759

Hong-Jian Du,Xu-Rong Cao,Hao-Jie Su,Xue-Qiang Chu,Hao Xu,Chengping Miao,Weidong Rao,Zhi-Liang Shen

引用次数: 0

Abstract

An efficient decarboxylative cross-coupling of zinc polyfluorobenzoate with aryl 2-pyridyl ester under palladium catalysis, which enabled the convenient access to valuable polyfluorinated aryl ketones, was developed. The cross-coupling reactions proceeded effectively to give an array of polyfluorinated aryl ketones in moderate to excellent yields with a reasonable substrate scope and broad functional group tolerance. In addition, a one-pot reaction with the use of in situ formed zinc polyfluorobenzoate commencing from polyfluorobenzoic acid and Zn(OH)2 could be accomplished as well in a step-economical fashion. Moreover, the coupling protocol could also be successfully subjected to scale-up synthesis and readily applied in the late-stage functionalization of biologically active complex molecules.

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钯催化的多氟苯甲酸锌与芳基2-吡啶酯脱羧交联制备多氟芳基酮。

研究了钯催化下多氟苯甲酸锌与芳基2-吡啶酯的高效脱羧交偶联反应，方便了制备有价值的多氟芳基酮。交叉偶联反应有效地进行，以中等至优异的收率得到一系列多氟芳基酮，具有合理的底物范围和广泛的官能团耐受性。此外，用多氟苯甲酸和Zn(OH)2原位生成的多氟苯甲酸锌进行一锅反应，也可以以阶梯经济的方式完成。此外，该偶联方案还可以成功地进行大规模合成，并易于应用于生物活性复合物分子的后期功能化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.