Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α-Amination of Stabilized Enolates
Diogo L. Poeira, Ana Cláudia R. Negrão, Hélio Faustino, Jaime A. S. Coelho, Clara S. B. Gomes, Pedro M. P. Góis, M. Manuel B. Marques
Abstract
A new family of hypervalent iodine reagents containing transferable primary amine groups is described. Benziodoxolone-based reagents were synthesized on the gram-scale through operationally simple reactions in up to quantitative yields. These bench-stable solids were characterized by X-ray analysis and successfully employed in the α-amination of indanone-based β-ketoesters in up to 83% yield. Mechanistic studies indicate a substitution mechanism involving an electrophilic amine.
Topics & Concepts
Hypervalent moleculeChemistryAminationReagentElectrophileAmine gas treatingElectrophilic aminationYield (engineering)IodineReactivity (psychology)Primary (astronomy)Combinatorial chemistryOrganic chemistrySubstitution reactionCatalysisMaterials scienceAstronomyPhysicsMedicinePathologyMetallurgyAlternative medicineOxidative Organic Chemistry ReactionsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods