Synthesis of Multideuterated (Hetero)aryl Bromides by Ag(I)-Catalyzed H/D Exchange

• DOI: 10.1021/acs.orglett.0c04139
• Publication Date: 2021-02-15T20:12:55Z
• Authors: Guang-Qi Hu; Jing-Wen Bai; En-Ci Li; Kai-Hui Liu; Fei-Fei Sheng; Hong-Hai Zhang
• Keywords: hetero; Chemical Sciences not elsewhere classified; transition-metal-catalyzed HIE process; bromides; Biophysics; D 2 O; Computational Biology; Biochemistry; 01 natural sciences; 0104 chemical sciences; multistep syntheses; Ag 2 CO 3; deuterium source; bioactive druglike molecules; Physical Sciences not elsewhere classified; Biotechnology

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 Ag2CO3 as catalyst and D2O 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.