Uncanonical Semireduction of Quinolines and Isoquinolines via Regioselective HAT-Promoted Hydrosilylation
Chao Hu, Cuong Vo, Rohan R. Merchant, Si-Jie Chen, Jonathan M. E. Hughes, Byron K. Peters, Tian Qin
Abstract
Heterocycles are the backbone of modern medical chemistry and drug development. The derivatization of "an olefin" inside aromatic rings represents an ideal approach to access functionalized saturated heterocycles from abundant aromatic building blocks. Here, we report an operationally simple, efficient, and practical method to selectively access hydrosilylated and reduced N-heterocycles from bicyclic aromatics via a key diradical intermediate. This approach is expected to facilitate complex heterocycle functionalizations that enable access to novel medicinally relevant scaffolds.
Topics & Concepts
ChemistryRegioselectivityDerivatizationHydrosilylationOlefin fiberBicyclic moleculeDiradicalCombinatorial chemistryAromaticityOrganic chemistryMoleculeCatalysisSinglet stateHigh-performance liquid chromatographyExcited statePhysicsNuclear physicsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis