Imine N^N^C-type pincer ligands were reacted with palladium(II) acetate and palladium(0) bis(dibenzylideneacetone) and the regioselective C-H and C-X activation was studied. C-X bonds that formed six-membered rings were selectively activated over C-H bonds; in addition sp 2 C-H bonds were selectively activated over sp 3 CH bonds. The formation and regioselectivity of the cyclometalated palladium(II) complexes were characterized by NMR, MS, and XRD. Photoluminescence studies of cyclopalladated complexes were conducted.