The Modular Synthesis of Sulfondiimidoyl Fluorides and their Application to Sulfondiimidamide and Sulfondiimine Synthesis
Mingyan Ding, Charles Bell, Michael C. Willis
Abstract
A modular synthesis of sulfondiimidoyl fluorides-the double aza-analogues of sulfonyl fluorides-allowing variation of the carbon and both nitrogen-substituents is reported. The chemistry uses readily available organometallic reagents, commercial sulfinylamines, simple electrophiles, and N-fluorobenzenesulfonimide (NFSI), as the starting materials. The reactions are broad in scope, efficient, and scalable. We show that the sulfondiimidoyl fluoride products can be combined with amines to provide sulfondiimidamides, and with organolithium reagents to provide sulfondiimines, and that reactivity in these transformations can be modulated by variation of the N-substituents.
Topics & Concepts
ElectrophileChemistryReagentCombinatorial chemistryFluorideModular designReactivity (psychology)SulfonylOrganic chemistryComputer scienceInorganic chemistryCatalysisProgramming languageAlkylPathologyMedicineAlternative medicineSynthesis and Catalytic ReactionsSynthesis of heterocyclic compoundsSynthesis and Biological Evaluation