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

Abstract

An operationally simple and green protocol using a NiSO 4 •6H 2 O/cationic 2,2′-bipyridyl ligand system as a watersoluble catalyst for the coupling of arylboronic acids with (2haloallyl)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.

Three‐Component Palladium‐Catalyzed Tandem Suzuki‐Miyaura/Allylic Substitution: A Regioselective Synthesis of (2‐Arylallyl) Aryl Sulfones

“…[17] Very recently, the same reaction has been described using nickel-catalysis in water. [23] However, under Pd-catalysis, the allylic Scheme 1. Previous preparations of terminal (2-arylallyl) aryl sulfones 1 and our approach.…”