Synthesis of Aryl Ketones by Cross-Coupling Reaction of Arylboronic Acids with Carboxylic Anhydrides in Aqueous Phase

Abstract

A highly efficient aqueous system of PdCl₂-catalyzed cross-coupling reaction of arylboronic acid with carboxylic anhydride (Suzuki-type reaction) without the use of phosphine ligands was developed. The reactions went smoothly in acetone/H₂O phase to give good yields of aryl ketones in short reaction times (1–3 h) at room temperature in air and were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic anhydrides.

Keywords:

• acetone
• aryl ketones
• boronic acids
• carboxylic anhydrides
• palladium catalysis

ACKNOWLEDGMENTS

I am grateful for the financial support provided by Dezhou University (No. 07RC001).

Notes

^a Reaction conditions: BA (benzoic anhydride, 1.0 mmol), PhB(OH)₂ (1.2 mmol), Na₂CO₃ (1.6 mmol), PdCl₂ (1.0 mol%), 1.5 h, rt.

^b Conversion was determined by GC using pantane-2,4-dione as an internal standard.

^c Reaction conducted under a nitrogen atmosphere.

^a Reaction conditions: BA (benzoic anhydride, 1.0 mmol), PhB(OH)₂ (1.2 mmol), base (1.6 mmol), catalyst (1.0 mol%), H₂O/acetone = 3:3 mL, 1.5 h, rt.

^b Conversion was determined by GC using pantane-2,4-dione as an internal standard.

^a Reaction conditions: benzoic anhydride (1.0 mmol), arylboronic acid (1.2 mmol), Na₂CO₃ (1.6 mmol), PdCl₂ (1.0 mol%), H₂O/acetone = 3:3 mL, 1.5 h, rt.

^b Isolated yield.

^a Reaction conditions: carboxylic anhydride (1.0 mmol), arylboronic acid (1.2 mmol), PdCl₂ (1.0 mol%), Na₂CO₃ (1.6 mmol), H₂O/acetone = 3:3 mL, 1.5 h, rt.

^b Isolated yield.