Synthesis of a palladium complex with a β-d-glucopyranosyl-thiosemicarbazone and its application in the Suzuki–Miyaura coupling of aryl bromides with phenylboronic acid

•Synthesis of a palladium complex with a β-d-glucopyranosyl-thiosemicarbazone.•Coordination to palladium via the azomethine nitrogen and the thiolate sulfur.•Efficient Suzuki–Miyaura coupling of aryl bromides in air.•Catalysis is mainly heterogeneous rather than homogeneous.

A palladium(II) complex with a known phosphane-free β-d-glucopyranosyl-thiosemicarbazone ligand has been prepared and characterized by spectroscopic studies. The ligand is bonded to the metal in a bidentate coordination mode via the azomethine nitrogen and the thiolate sulfur in the dimeric form. The application of this complex on the Suzuki–Miyaura coupling of aryl bromides with phenylboronic acid in DMF/K2CO3 at 100 °C for 24 h in air, using 0.1 mol% of palladium, afforded the corresponding biaryls in 54–91% yield. Crabtree’s test provided evidence that the real catalyst is mainly heterogeneous rather than homogeneous.

Graphical abstractA palladium(II) complex with a β-d-glucopyranosyl-thiosemicarbazone ligand has been prepared as a dimer in a bidentate fashion via the azomethine nitrogen and the thiolate sulfur. This complex efficiently catalyzes the Suzuki–Miyaura coupling of aryl bromides with phenylboronic acid in air. Catalysis is mainly heterogeneous rather than homogeneous.Figure optionsDownload full-size imageDownload as PowerPoint slide