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Regioselective Deuteration of Arenes Enabled by Simple Heterogeneous Palladium Catalysis

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

2023The Journal of Organic Chemistry11 citationsDOI

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 2 )–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.

Topics & Concepts

RegioselectivityPalladiumCatalysisDeuteriumChemistryCombinatorial chemistryMoleculeHeterogeneous catalysisOrganic chemistryPhysicsQuantum mechanicsChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisAmmonia Synthesis and Nitrogen Reduction
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