Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
Thomas Sephton, Jonathan M. Large, Sam Butterworth, Michael F. Greaney
Abstract
Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherwise inaccessible by traditional SNAr chemistry. The reaction highlights the distinct reactivity of the sulfinamide group in Smiles rearrangements versus that of the more common sulfonamides.
Topics & Concepts
Smiles rearrangementChemistrySteric effectsNucleophilic aromatic substitutionCombinatorial chemistryReactivity (psychology)Sequence (biology)StereochemistryOrganic chemistryNucleophilic substitutionBiochemistryAlternative medicineMedicinePathologySulfur-Based Synthesis TechniquesPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Catalytic Reactions