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TCI Practical Example: Metathesis Reaction Using the Ruthenium-Indenylidene Catalyst
We are proud to present the ring-closing metathesis using the ruthenium-indenylidene complex.
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Used Chemicals
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Procedure
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To a solution of diethyl diallylmalonate (1.20g, 5.0 mmol) in dichloromethane (50 mL), (3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II) dichloride (0.09 g, 0.1 mmol, 2 mol%) was added at room temperature under N2 atmosphere. After stirring the reaction solution for 1 hour, the solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:ethyl acetate = 1:0 - 99:1 - 9:1) to give compound 1 as a pale yellow liquid (0.78 g, 74%).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (hexane:ethyl acetate = 9:1, Rf = 0.33) and NMR (CDCl3).
Dichloromethane was degassed by bubbling with N2 gas for 30 min.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3); δ 5.54 (s, 2H), 4.13 (q, 4H, J = 6.7 Hz), 2.94 (s, 4H), 1.18 (t, 6H, J = 8.0 Hz).
13C NMR (101 MHz, CDCl3); δ 172.08, 127.66, 61.37, 58.64, 40.67, 13.87.
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Lead Reference
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- Indenylidene Ruthenium Complex Bearing a Sterically Demanding NHC Ligand: An Efficient Catalyst for Olefin Metathesis at Room Temperature
