Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergistic Innovation Center for Advanced Materials (SICAM), Nanjing Tech. University (Nanjing Tech.), 30 Puzhu Road, Nanjing 211816, P.R. China.
Org Lett. 2021 Mar 5;23(5):1554-1560. doi: 10.1021/acs.orglett.0c04139. Epub 2021 Feb 15.
Deterium-labeled (hetero)aryl bromide is one of the most widespread applicable motifs to achieve important deuterated architectures for various scientific applications. Traditionally, these deterium-labeled (hetero)aryl bromides are commonly prepared via multistep syntheses. Herein, we disclose a direct H/D exchange protocol for deuteration of (hetero)aryl bromides using AgCO as catalyst and DO as deuterium source. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of over 55 (hetero)aryl bromides including bioactive druglike molecules and key intermediates of functional materials. In addition, this method showed distinguishing site-selectivity toward the existing transition-metal-catalyzed HIE process, leading to multideuterated (hetero)aryl bromides in one step.
氘标记的（杂）芳基溴化物是实现各种科学应用中重要氘代结构的最广泛应用的基序之一。传统上，这些氘标记的（杂）芳基溴化物通常通过多步合成制备。在此，我们公开了一种使用 AgCO 作为催化剂和 DO 作为氘源的直接 H/D 交换协议，用于（杂）芳基溴化物的氘化。该协议高效、操作简单，适用于超过 55 种（杂）芳基溴化物的氘标记，包括生物活性类似物药物分子和功能材料的关键中间体。此外，该方法对现有的过渡金属催化 HIE 过程表现出明显的位点选择性，可一步得到多氘代（杂）芳基溴化物。
