Halogen-Bond-Induced Consecutive C<sub>sp</sub><sup>3</sup>–H Aminations via Hydrogen Atom Transfer Relay Strategy
Fan Wu, Jeewani P. Ariyarathna, Navdeep Kaur, Nur‐E Alom, Maureen L. Kennell, Omar H. Bassiouni, Wei Li
Abstract
The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3–H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.
Topics & Concepts
ChemistryHalogenAminationHalogen bondIntermolecular forcePyrrolidineHydrogen bondHydrogen atomAtom (system on chip)Non-covalent interactionsCombinatorial chemistryPhotochemistryMoleculeMedicinal chemistryOrganic chemistryCatalysisGroup (periodic table)Computer scienceEmbedded systemAlkylSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsPhenothiazines and Benzothiazines Synthesis and Activities