Synthetic Strategy for Unsymmetrical α-Fluoro-α′-aryl Ketones

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-13 DOI:10.1021/acs.orglett.4c04486

Shubham Dutta, Avijit Maity, Shengwen Yang, Rajendra K. Mallick, Manash P. Gogoi, Vincent Gandon, Akhila K. Sahoo

引用次数: 0

Abstract

α-Fluoro-α′-aryl ketones are crucial in pharmaceuticals and agrochemicals. However, synthesizing unsymmetrical α-fluoro-α′-aryl ketones poses regioselective challenges. This study presents a one-pot aryl-oxy-fluorination method for synthesizing such unsymmetrical fluoro-aryl ketones. Using ynamide, aryl boronic acid, and F-source under Pd-catalysis, this method efficiently produces a wide range of valuable α-fluoro-α′-aryl ketones with potential applications. Through a combination of control experiments and DFT studies, we proposed a reaction mechanism involving in situ acetic acid formation.

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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.