Mesoionic Carbene–Iridium Complex Catalyzed<i>Ortho</i>-Selective Hydrogen Isotope Exchange of Anilines with High Functional Group Tolerance
Wei Liu, Lei Cao, Zengyu Zhang, Gang Zhang, Shiqing Huang, Linwei Huang, Peng Zhao, Xiaoyu Yan
Abstract
Mesoionic carbene–iridium complex 1a has been investigated in the hydrogen isotope exchange (HIE) reaction of anilines. By employing 1 mol % of 1a as catalyst, anilines were selectively deuterated at the ortho-position with high deuteration levels. High ortho-selectivity was observed for anilines with various competing directing groups, which is in contrast with catalytic results of Kerr’s catalysts.
Topics & Concepts
MesoionicIridiumChemistryCarbeneCatalysisDeuteriumKinetic isotope effectMedicinal chemistrySpin isomers of hydrogenSelectivityHydrogen isotopeHydrogenPhotochemistryOrganic chemistryQuantum mechanicsPhysicsChemical Reactions and IsotopesMuon and positron interactions and applicationsAsymmetric Hydrogenation and Catalysis