Citation: Yunhao Guan, Xia Peng, Rong Fan, Xiaoying Feng, Hongguang Du, Jiajing Tan. Precise synthesis of ortho-deuterated aromatic derivatives: An arylthianthrenium salt-based platform approach[J]. Chinese Chemical Letters, ;2026, 37(1): 111132. doi: 10.1016/j.cclet.2025.111132 shu

Precise synthesis of ortho-deuterated aromatic derivatives: An arylthianthrenium salt-based platform approach

Department of Organic Chemistry, Beijing University of Chemical Technology, Beijing 100029, China

dhg@mail.buct.edu.cn

jiajing.tan@foxmail.com

Received Date: 17 December 2024
Revised Date: 11 March 2025
Accepted Date: 20 March 2025
Available Online: 21 March 2025

Figures(4)

The deuterium labeling has garnered significant interest in drug discovery due to its critical role on improving pharmacokinetic and metabolic properties. However, despite its pharmaceutical value, the general and rapid syntheses of aromatic scaffolds that contains deuterium remain an important yet elusive task. State-of-the-art approaches mainly relied on the transition metal-catalyzed C–H deuteration via the assistance of directing groups (DGs), which often suffered from over-deuteration and lengthy step counts required for installation and/or removal of DG. Herein, we report a generalizable synthetic linchpin strategy for the facile preparation of the ortho-deuterated aromatic core. Through capture of aryne-derived 1,3-zwitterion with heavy water, we synthesized an array of ortho-deuterated aryl sulfonium salts. These novel linchpins not only participated the transition metal catalyzed cross-coupling reaction as nucleophiles, but also served as aryl radical reservoirs under photochemical or electrochemical conditions, enabling facile and precise access to structurally diverse deuterated aromatics. Moreover, we have disclosed a novel EDA complex enabled direct arylation of phosphines under visible-light irradiation, further expanding the utility of our platform approach.
- Deuterium labeling,
- Thianthrenium salts,
- Precise synthesis,
- Linchpin strategy,
- Aryne chemistry,
- Organosulfur chemistry
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