Phosphane-free C–C Heck couplings catalyzed by Pd(II) fluorinated aniline complexes of the type trans-[PdCl2(NH2ArF)2]

A series of palladium fluoro-aniline complexes of the trans-[PdCl2(NH2ArF)2] type were synthesized in good yields by direct reaction of trans-[PdCl2(C6H5CN)] with ArFNH2; ArF = C6H3-2,3-F2 (1), C6H3-2,5-F2 (2), C6H3-3,4-F2 (3), C6H3-3,5-F2 (4), C6H2-2,3,4-F3 (5), C6H2-2,3,6-F3 (6), C6H2-2,4,5-F3 (7), C6H2-2,4,6-F3 (8), C6F4-4-H (9), C6F5 (10). The crystal structures of complexes 3, 4 and 5 were determined. Heck coupling reactions were carried out using complexes 1–10 as catalysts in order to examine the effect of the fluorinated anilines in the reaction of bromobenzene and styrene.

Graphical abstractA series of palladium complexes of the type trans-[PdCl2(NH2ArF)2] were synthesized and the effect of the fluorinated aniline ligands in the catalytic performance of these complexes examined in the Heck coupling reaction. Figure optionsDownload full-size imageDownload as PowerPoint slide