Trisulfur-Radical-Anion-Triggered C(sp<sup>2</sup>)–H Amination of Electron-Deficient Alkenes
Khang X. Nguyen, Phuc H. Pham, Thao Nguyen, Chou‐Hsun Yang, Hoai T. B. Pham, Tung T. Nguyen, Haobin Wang, Nam T. S. Phan
Abstract
A trisulfur-radical-anion (S3̇–)-triggered C(sp2)–H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3̇– initiates the nucleophilic attacks via a thiirane intermediate.
Topics & Concepts
ChemistryAminationNucleophileSelectivityIonMedicinal chemistryThiiraneReductive aminationStereochemistryOrganic chemistryCatalysisRing (chemistry)Synthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques