The authors of this work have optimized a novel synthetic route towards glucose-based PdII-bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6-iodo-glucopyranosides, followed by acyl-protection, then quaternization with imidazoles and finally the conversion of these acyl-protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl-protected glucosyl imidazolium iodides as NHC-precursors and 15 complexes have been synthesized. The structure-activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki-Miyaura between bromobenzene and 4-tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

中文翻译：

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模型 Suzuki-Miyaura 反应中葡萄糖基 PdII-Bis(NHC) 配合物的构效关系

这项工作的作者优化了一种基于葡萄糖的 PdII-bis(NHC) 配合物的新型合成路线，仅需 4 个步骤，总产率高达 73%。合成路线包括对 6-碘-吡喃葡萄糖苷进行 Appel 反应，然后进行酰基保护，然后用咪唑季铵化，最后将这些酰基保护的葡萄糖基咪唑鎓盐转化为其各自的钯 (II) 双 (NHC) 络合物，通过中间银(I)络合物。总体而言，已合成了 11 种酰基保护的葡萄糖基咪唑碘化物作为 NHC 前体和 15 种配合物。研究了这些配合物中不同官能团的结构-活性关系及其在溴苯和 4-甲苯硼酸反应之间的 Suzuki-Miyaura 模型中的反应性，并研究了在 0.005 mol% 催化负载量下产生 >99% 产率的高反应性配合物被发现了。