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TCI Practical Example: Sonogashira Cross Coupling with PdCl2(PPh3)2 as a Catalyst
We would like to introduce the Sonogashira cross coupling of iodobenzene and ethynylbenzene using a palladium catalyst.
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Used Chemicals
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Procedure
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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 %).
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Experimenter's Comments
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The reaction mixture was monitored by GC.
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Analytical Data
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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.
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Other References
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- A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines
