Tandem Pd-Catalyzed Intermolecular Allylic Alkylation/Allylic Dearomatization Reaction of Benzoylmethyl pyridines, Pyrazines, and Quinolines

An efficient synthesis of nitrogen-containing heterocycles via Pd-catalyzed tandem allylic alkylation and dearomatization reactions was reported. In this reaction design, heteroarenes such as pyridines, pyrazines, and quinolines serve as bis-nucleophiles by installing a benzoyl group at the C2 benzylic position. With but-2-ene-1,4-diyl dimethyl dicarbonate as the bis-electrophile, the tandem Pd-catalyzed intermolecular allylic alkylation/allylic dearomatization reaction of benzoylmethylsubstituted heteroarenes has been developed. 2,3-Dihydroindolizine, 6,7-dihydropyrrolo[1,2-c]pyrazine, and 1,2-dihydropyrrolo[1,2-a]quinolin derivatives were obtained in moderate to good yields.