Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction
Dmitrii A. Shabalin, Maxim K. Kazak, Igor А. Ushakov, Alexander V. Vashchenko, Elena Yu. Schmidt
Abstract
]isoquinolinium salts from 1-pyrrolines and alkynes through rhodium-catalyzed C-H functionalization/N-annulation tandem reaction is described. The protocol features a good substrate tolerance, mild reaction conditions, and high yields of target products. Exploration of the alkyne scope unexpectedly revealed a novel labile functional group-promoted rhodium-catalyzed C-H functionalization/C-annulation/elimination cascade reaction of 1-pyrrolines with electron-deficient alkynes.
Topics & Concepts
AnnulationChemistryRhodiumTandemSurface modificationCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryStereochemistryComposite materialMaterials sciencePhysical chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsFluorine in Organic Chemistry