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简单多相钯催化实现芳烃的区域选择性氘代反应

Regioselective Deuteration of Arenes Enabled by Simple Heterogeneous Palladium Catalysis.

作者信息

Wang Qiuzhu, Xiao Wenjuan, He Honghui, Guo Jie, Wang Mengning, Ma Mengtao, Zhao Binlin

机构信息

Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.

State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.

出版信息

J Org Chem. 2023 Aug 4;88(15):10818-10827. doi: 10.1021/acs.joc.3c00902. Epub 2023 Jul 24.

Abstract

A heterogeneous redox-neutral palladium-catalytic platform was reported for the preparation of deuterated (hetero) arenes from (hetero) arenes mediated by regioselective C(sp)-H thianthrenation utilizing commercially available and recyclable Pd/C catalyst. A wide range of deuterated compounds could be obtained in high yields with excellent levels of deuterium incorporation under these simple heterogeneous catalytic conditions with the requirement of stable and easily handled DCOONa as a deuterium source. The late-stage deuteration of pharmaceuticals and bioactive molecules was also achieved by this approach.

摘要

报道了一种多相氧化还原中性钯催化平台,用于在市售且可回收的钯/碳催化剂介导下,通过区域选择性C(sp)-H噻蒽化反应,从(杂)芳烃制备氘代(杂)芳烃。在这些简单的多相催化条件下,以稳定且易于处理的DCOONa作为氘源,可高产率获得多种氘代化合物,且氘掺入水平优异。该方法还实现了药物和生物活性分子的后期氘代。

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