Cu(OAc)₂-Catalyzed N-Arylation of Sulfonamides with Arylboronic Acids or Trimethoxy(phenyl)silane

Abstract

Cu(OAc)₂-catalyzed C-N bond-formation reaction of sulfonamides with organoboronic acids or trimethoxy(phenyl)silane was achieved in the presence of 20 mol% of Cu(OAc)₂, providing N-arylation products with yields ranging from moderate to good.

Keywords:

• Arylboronic acids
• Cu(OAc)₂-catalyzed
• sulfonamides
• trimethoxy(phenyl)silane

ACKNOWLEDGMENTS

We thank the National Natural Science Foundation of China (No. 20504023) and the Science and Technology Projects of Zhejiang Province (No. 2006C31030) for financial support.

Notes

^a Reaction conditions: 4-methylbenzenesulfonamide (0.2 mmol), phenylboronic acid (0.3 mmol), base (0.3 mmol), solvent (2 mL), 90 °C, 12 h.

^a All reactions were run with sulfonamides (0.2 mmol), arylboronic acids (0.3 mmol), Cu(OAc)₂ (7.4 mg, 20 mol%), and K₂CO₃ (0.3 mmol) in 2 mL dry isopropanol at 90 °C in a sealed tube for 12 h.