Palladium(0) complexes of (P,P) and (P,N) ligands immobilized on silica gel as catalysts in selective Heck type carbon–carbon coupling reactions

Pd(0) complexes of Ph2P–N–PPh2 and (P,N) ligands anchored on silica gel via a –O–Si–CH2CH2CH2– linker are shown to catalyze C–C coupling reactions between aryl bromides/aryl iodides, p-Y–C6H4X (where Y = NO2, Cl; X = Br, I) and acrylic acid/styrene CH2CHR (R = Ph, COOH) in good yield, up to 92%. Only the trans product is formed selectively. The catalysts can be re-used up to 15–16 times, without significant loss of yield. Their further re-use up to 30 times is also possible, but with the yield reduced by 10–15%.

Graphical abstractPd(0) complexes of Ph2P–N–PPh2 and (P,N) ligands anchored on silica gel (1–3) are shown to catalyze C–C coupling reactions between aryl bromides/aryl iodides, p-Y–C6H4X (where Y = NO2, Cl; X = Br, I) and acrylic acid/styrene CH2CHR (R = Ph, COOH). Only the trans product is formed selectively. The catalysts can be reused up to 15–16 times, without significant loss of yield.Figure optionsDownload full-size imageDownload as PowerPoint slide