(3-Phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II) Dichloride

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.

References

• A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 1999, 64, 8275.
• A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738.
• A. Fürstner, O. Guth, A. Düffels, G. Seidel, M. Liebl, B. Gabor, R. Mynott, Chem. Eur. J. 2001, 7, 4811.