Wright Jay S, Ma Richard, Webb E William, Winton Wade P, Stauff Jenelle, Cheng Kevin, Brooks Allen F, Sanford Melanie S, Scott Peter J H
Department of Radiology, University of Michigan, Ann Arbor, MI-48109, USA.
Department of Chemistry, University of Michigan, Ann Arbor, MI-48109, USA.
Angew Chem Int Ed Engl. 2024 Jan 8;63(2):e202316365. doi: 10.1002/anie.202316365. Epub 2023 Dec 8.
This report describes the development of a Zn(OTf) -mediated method for converting α-tertiary haloamides to the corresponding fluorine-18 labelled α-tertiary fluoroamides with no-carrier-added [ F]tetramethylammonium fluoride. 1,5,7-Triazabicyclo[4.4.0]dec-5-ene is an essential additive for achieving high radiochemical conversion. Under the optimised conditions, radiofluorination proceeds at sterically hindered tertiary sites in high radiochemical conversions, yields, and purities. This method has been successfully automated and applied to access >200 mCi (>7.4 GBq) of several model radiofluorides. Mechanistic studies led to the development of a new, nucleophilic C-H radiofluorination process using N-sulphonyloxyamide substrates.
本报告描述了一种锌（三氟甲磺酸盐）介导的方法，该方法可将α-叔卤代酰胺转化为相应的无载体添加的[¹⁸F]四甲基氟化铵标记的α-叔氟酰胺。1,5,7-三氮杂双环[4.4.0]癸-5-烯是实现高放射化学转化率的关键添加剂。在优化条件下，放射性氟化反应在空间位阻较大的叔位以高放射化学转化率、产率和纯度进行。该方法已成功实现自动化，并应用于制备超过200 mCi（>7.4 GBq）的几种放射性氟化物模型。机理研究促成了一种使用N-磺酰氧基酰胺底物的新型亲核C-H放射性氟化过程的开发。
