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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.

Used Chemicals

• Diethyl Diallylmalonate [D1183]
• (3-Phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II) Dichloride [P2004]
• Dichloromethane

Procedure

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%).

Experimenter’s Comments

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.

Analytical Data

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.

Lead Reference

• Indenylidene Ruthenium Complex Bearing a Sterically Demanding NHC Ligand: An Efficient Catalyst for Olefin Metathesis at Room Temperature
• H. Clavier, C. A. Urbina-Blanco, S. P. Nolan, Organometallics 2009, 28, 2848.