Synthesis of Biaryls via Pd-Catalyzed Decarboxylative Coupling of Substituted Benzoic Acids with Phenylboronic Acids

Abstract

A Pd-catalyzed decarboxylative coupling of substituted benzoic acids with phenylboronic acid has been developed. Under the optimized conditions, a variety of substituted benzoic acids were found to undergo decarboxylative coupling with various phenylboronic acids to give the desired unsymmetrical biaryls in good yields.

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GRAPHICAL ABSTRACT

Keywords:

• Benzoic acids
• biaryls
• cross-coupling
• decarboxylative
• palladium-catalyzed
• phenylboronic acid

Notes

^a All reactions were carried under dry nitrogen atmosphere at 130 °C for 12 h.

^b Yields were determined by GC.

^a All reactions were carried out under dry nitrogen atmosphere using 10 mol% PdCl₂, 3 equiv Ag₂CO₃, and 20 mol% PPh₃ in DMSO/DMF (9/1, 6 mL/mmol) at 130 °C for 12 h.

^b Isolated yields.