Palladium-Catalyzed 1,2-Carboamination of Acrylamides via Anti-Michael-Type Addition.

Abstract

Herein, we report a palladium-catalyzed 1,2-carboamination of acrylamides via anti-Michael-type addition. The protocol enables reverse regioselective functionalization of activated alkenes using carbazole derivatives as nucleophiles and aryl, vinyl, and alkyl iodide derivatives as electrophiles under mild reaction conditions. The three-component carboamination reaction proceeds via the simultaneous formation of C-C and C-N bonds, furnishing structurally diverse carboaminated products in moderate to excellent yields, with broad substrate scope and functional-group tolerance. Preliminary mechanistic studies suggest directed alkene activation by Pd(II), followed by anti-nucleopalladation to generate a proposed alkyl-Pd(II) intermediate, which subsequently undergoes coupling with aryl iodides to furnish the desired products. This work expands the scope of anti-Michael-type alkene functionalization and provides efficient access to structurally diverse nitrogen-containing molecules.