Maji Sudip, Basuli Suchand, Banerjee Subhrashis, Pradhan Deepak R, Hirschi Jennifer S, Vetticatt Mathew J
Department of Chemistry, Binghamton University, Vestal, NY 13850, USA.
Res Sq. 2025 Aug 4:rs.3.rs-7216247. doi: 10.21203/rs.3.rs-7216247/v1.
Most practical fluorination reagents deliver a fluorine atom either as a nucleophile (F) or as an electrophile (F). In contrast, bench-stable radical fluorine (F) reagents are relatively less common and the vast majority of 'radical fluorinations' involve reactions of carbon-centered radicals with electrophilic fluorination reagents. Here, we disclose that silver (II) fluoride (AgF) in acetonitrile is a mild source of F that can be leveraged for the synthesis of a variety of high-value organofluorine compounds from abundantly available reactants such as alkanes, alkenes, and carboxylic acids, as well as from pharmaceutically relevant heterocycles such as indoles and benzofurans. This platform technology obviates the need for expensive catalysts and fluorinating reagents that are typically necessary to accomplish these transformations and relies on the use of AgF in acetonitrile as the sole reagent under mild conditions.
大多数实用的氟化试剂提供的氟原子要么作为亲核试剂(F⁻),要么作为亲电试剂(F⁺)。相比之下,在实验室条件下稳定的自由基氟(F•)试剂相对较少见,并且绝大多数“自由基氟化反应”涉及碳中心自由基与亲电氟化试剂的反应。在此,我们揭示乙腈中的氟化银(II)(AgF₂)是一种温和的F•来源,可用于从大量可得的反应物(如烷烃、烯烃和羧酸)以及药学相关的杂环化合物(如吲哚和苯并呋喃)合成各种高价值的有机氟化合物。这种平台技术无需使用通常完成这些转化所需的昂贵催化剂和氟化试剂,而是在温和条件下仅依靠使用乙腈中的AgF₂作为唯一试剂。