McIntee Jason W, Sundararajan Chitra, Donovan Amanda C, Kovacs Michael S, Capretta Alfredo, Valliant John F
Department of Chemistry, McMaster University, Hamilton, Ontario, Canada L8S 4M1.
J Org Chem. 2008 Nov 7;73(21):8236-43. doi: 10.1021/jo8013287. Epub 2008 Oct 1.
A convenient method for the preparation of fluorous aryl stannanes was developed as a means of expanding the general utility of the fluorous labeling strategy (FLS). Following the synthesis of a novel fluorous distannane, a palladium-catalyzed cross-coupling reaction was used to prepare the target compounds from aryl halides. The scope of the reaction was investigated by preparing a small library of model compounds where the reaction yields were similar to those reported for the analogous procedures employing hexamethyl- or hexabutyldistannanes. The utility of the reported methodology was demonstrated through the successful synthesis of fluorous precursors to two established molecular imaging and therapy agents (FIAU, IUdR). These were radiolabeled with iodine-125 and the desired products isolated in high yield and effective specific activity.
开发了一种制备氟代芳基锡烷的简便方法，作为扩展氟代标记策略（FLS）通用效用的一种手段。在合成一种新型氟代二锡烷之后，利用钯催化的交叉偶联反应由芳基卤化物制备目标化合物。通过制备一个小型模型化合物库来研究反应范围，其中反应产率与采用六甲基或六丁基二锡烷的类似方法所报道的产率相似。通过成功合成两种已确立的分子成像和治疗剂（FIAU、IUdR）的氟代前体，证明了所报道方法的实用性。这些前体用碘 - 125进行放射性标记，所需产物以高产率和有效的比活度分离得到。
