Palladium-Catalyzed Synthesis of C-1 Deuterated Aldehydes from (Hetero) Arenes Mediated by C (sp2)–H Thianthrenation

• DOI: 10.1021/acs.orglett.2c02328
• Publication Date: 2022-07-26T13:06:31Z
• Authors: Binlin Zhao; Qiuzhu Wang; Tianxiang Zhu; Bin Feng; Mengtao Ma
• Keywords: Aldehydes; Deuterium; Oxidation-Reduction; 01 natural sciences; Palladium catalysis; Catalysis; Palladium; 0104 chemical sciences

A palladium-catalyzed deuterated formylation of aryl sulfonium salts is prepared conveniently from readily available arenes, which enables the expedient synthesis of a series of structurally diverse C-1 deuterated aldehydes with 96%-99% deuterium incorporation. The easy to handle and cost-effective DCOONa provides a deuterium source, which can be introduced onto the formyl units with excellent selectivity under the palladium-catalytic redox neutral conditions. This catalytic route can accomplish the direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C (sp2)-H thianthrenation. Moreover, on the basis of this practical approach, several deuterated drugs and analogues could be prepared with excellent levels of deuterium incorporation.