Palladium catalyzed N-H bond insertion and intramolecular cyclization cascade: the divergent synthesis of heterocyclics

The palladium catalyzed carbenoid based N-H insertion and electronic effect controlled 5-exo-trig or 6-endo-trig mode Heck cyclization in one-pot has been realized for ortho-iodoanilines, in which PdCl2 was used as the single palladium resource. The corresponding indoles and quinolines were obtained respectively. However, for ortho-triflateanilines, base promoted cyclization is preferred and the lactones were obtained.