Complex of 2-(methylthio)aniline with palladium(II) as an efficient catalyst for Suzuki–Miyaura C-C coupling in eco-friendly water

Graphical abstract: - Highlights: • Synthesis of palladium complex of a bidentate ligand of (N, S) type. • Determination of single crystal structure of the complex. • Complex showed excellent activity for Suzuki–Miyaura coupling reactions in water. • TON values up to 93,000 were achieved. - Abstract: 2-(Methylthio)aniline (L1), a bidentate (S,N) ligand synthesized by the reaction of o-aminothiophenol with methyl iodide, on reacting with Na2PdCl4 in acetone and water gives a complex [PdL1Cl2] (1). Single crystal X-ray diffraction studies have revealed that the geometry of palladium in 1 is nearly square-planar and the ligand L1 is bound to the palladium through S and N in a bidentate coordination mode forming a five membered chelate ring. This complex functions as a thermally and air stable catalyst of high efficiency for Suzuki–Miyaura C-C coupling reactions in water. It catalyzes C-C coupling between various aryl bromides and phenylboronic acid under mild reaction conditions in water. TON value up to 93,000 has been obtained