Nickel-Catalyzed Alkynylation of Aryl Iodides (Sonogashira Reaction) in Water

Abstract

The Sonogashira coupling of terminal acetylenes with aryl iodides, catalyzed by Ni-Cu, in the presence of sodium lauryl sulfate as the surfactant and cesium carbonate as the base, in water, leads to the formation of aryl alkyne products.

Keywords:

• Alkynylation
• aryl iodide
• nickel catalyst
• Sonogashira reaction

ACKNOWLEDGMENTS

The authors thank the Research Council of Shahrood University of Technology for the support of this work.

Notes

^a Reaction conditions: iodobenzene (1.0 mmol), 1-hexyne (1.5 mmol), Ni(PPh₃)₂Cl₂ (0.01 mmol), CuI (0.02 mmol), sodium lauryl sulfate (0.07 mmol), base (2.0 mmol), and degassed water (5 mL) at 60°C for 4 h under Ar.

^b GC yields.

^a Reaction conditions: iodobenzene (1.0 mmol), 1-hexyne (1.50 mmol), Cs₂CO₃ (2.0 mmol), and degassed water (5 mL) at 60°C for 4 h under Ar.

^b GC yields.

^c Reaction time: 2 h.

^d Reaction time: 7 h.

^a Reaction conditions: 1 (1.0 mmol), 2 (1.5 mmol), Ni(PPh₃)₂Cl₂ (0.01 mmol), CuI (0.02 mmol), sodium lauryl sulfate (0.07 mmol), Cs₂CO₃ (2.0 mmol), and degassed water (5 mL) at 60°C under Ar.

^b GC yields.