K<sub>2</sub>CO<sub>3</sub>/18-Crown-6-Catalyzed Selective H/D Exchange of Heteroarenes with Bromide as a Removable Directing Group
Jianguo Gu, Caixia Wang, Guang-Qi Hu, Kang Shen, Honghai Zhang
Abstract
/18-crown-6-catalyzed H/D exchange of heretoarenes in high atom % deuterium incorporation is disclosed. The use of a weak base as a catalyst leads to excellent site selectivity and broad functional group tolerance. Control experiments indicated that the use of bromide, which enhances the adjacent C-H bond reactivity, as a removable directing group is essential. Moreover, conversion of bromide to other functional groups is also performed to construct other useful deuterated compounds.
Topics & Concepts
ChemistryBromideCatalysisFunctional groupDeuteriumReactivity (psychology)Group (periodic table)SelectivityBase (topology)Weak base18-Crown-6Medicinal chemistryMoleculeOrganic chemistryPhysicsQuantum mechanicsAlternative medicineMathematical analysisMedicinePathologyPolymerMathematicsChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis