Nickel-Catalyzed Suzuki–Miyaura Coupling in Water for the Synthesis of 2‑Aryl Allyl Phosphonates and Sulfones

An operationally simple and green protocol using a NiSO4·6H2O/cationic 2,2′-bipyridyl ligand system as a water-soluble catalyst for the coupling of arylboronic acids with (2-haloallyl)­phosphonates and (2-haloallyl)­sulfones in water under air was developed. The reaction was performed at 120 °C with arylboronic acids (2 mmol) and (2-haloallyl)­phosphonates or sulfones (1 mmol) in the presence of 5 mol % of the Ni catalytic system in a basic aqueous solution for 1 h, giving the corresponding 2-aryl allyl phosphonates or sulfones in good to excellent yields. This reaction features the use of an abundant transition metal as a catalyst in water and exhibits high functional group tolerance, rendering it an eco-friendly procedure.