piperidines and 2-phenylquinoline

Hydrogen and deuterium gas were produced and directly applied in a two-chamber system. These gaseous reagents were generated by the simple reaction of metallic zinc with HCl in water for H2 and DCl in deuterated water for D2. The setup proved efficient in classical Pd-catalyzed reductions of ketones, alkynes, alkenes, etc. in near-quantitative yields. The method was extended to the synthesis and isotope labeling of quinoline and 1,2,3,4-tetrahydroquinoline derivatives. Finally, CX-546 and Olaparib underwent efficient Ir-catalyzed hydrogen isotope exchange reactions.

Topics: Alkenes; Alkynes; Catalysis; Deuterium; Dioxanes; Dioxoles; Hydrogen; Isotope Labeling; Kinetics; Metals; Oxidation-Reduction; Phthalazines; Piperazines; Piperidines; Quinolines