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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 16
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Original Articles

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

Pages 2826-2837 | Received 10 Nov 2007, Published online: 25 Aug 2010
 

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.

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.

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