Amine-Mediated Transimination and Aromatization-Triggered Domino Reaction in the Synthesis of Polyfunctionalized 4-Aminoquinolines.

Dearomatization provides numerous possibilities for the development of new transformative modes of aromatic compounds. A conceptually novel metal-free multicomponent domino reaction of the dearomatized products of 2-alkynylanilines is developed. The reaction involves the secondary amine-mediated transimination with α-amino nitriles and subsequent aromatization-triggered cascade rearrangement, nucleophilic cyclization, and retro-Strecker reaction. This process provided a new practical method for the rapid synthesis of polyfunctionalized 4-aminoquinolines from readily available starting materials.

Direct assembly of 3,4-difunctionalized benzofurans and polycyclic benzofurans by phenol dearomatization and palladium-catalyzed domino reaction.

A method to directly convert 2-alkynylphenols to 3,4-difunctionalized benzofurans and polycyclic benzofurans was developed. This protocol involves a hypervalent-iodine-mediated oxidative dearomatization to break the aromaticity of 2-alkynylphenols, and a palladium-catalyzed domino reaction to install two functional groups at the C3 and the C4 positions and restore the aromaticity of benzofurans.