Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution
Damian Antoniak, Michał Barbasiewicz
Abstract
H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.
Topics & Concepts
ChemistryCarbanionSubstituentAlkylationNucleophileAdductSteric effectsElectrophileSulfonylMedicinal chemistryIsopropylNitroSubstitution reactionAlkylStereochemistryOrganic chemistryCatalysisChemical Reaction MechanismsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques