APPLICATION
TCI Practical Example: Sonogashira Cross Coupling
Used Chemicals
Iodobenzene [I0050]
Ethynylbenzene [E0196]
Bis(triphenylphosphine)palladium(II) Dichloride [B1667]
Copper(I) Iodide [C2163]
Triethylamine [T0424]
Tetrahydrofuran Anhydrous [T2394]
Procedure
To a two-necked flask was charged with iodobenzene (1.09 mL, 9.80 mmol, 1.0 equiv.), ethynylbenzene (1.18 mL, 10.7 mmol, 1.1 equiv.), bis(triphenylphosphine)palladium(II) dichloride (137 mg, 0.195 mmol 2.0 mol%), copper(I) iodide (40 mg, 0.210 mmol, 2.1 mol%), tetrahydrofuran anhydrous (40 mL), triethylamine (1.90 mL, 14.7 mmol, 1.5 equiv.) under nitrogen atmosphere. The mixture was stirred at room temperature for 1.5 h. The reaction mixture was quenched with water (20 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and then concentrated under reduce pressure. The crude was purified by column chromatography on silica gel (hexane) to afford diphenylacetylene as a white powder (1.70 g, 97 %).
Experimenter’s Comments
The reaction mixture was monitored by GC.
Analytical Data
Diphenylacetylene
1H NMR (400 MHz, CDCl3); δ 7.51-7.54 (m, 4H), 7.31-7.35 (m, 6H).
13C NMR (101 MHz, CDCl3); δ 131.6, 128.3, 128.2, 123.2, 89.3.
Other References
A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines
K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467.
Application
One-pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes
QUALITY CERTIFICATION / COMPLIANCE
Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).
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