1-Hydroxytetraphenylcylclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-mu-hydrotetracarbonyldiruthenium(II)

Reviews

Shvo's diruthenium complex: a robust catalyst

• R. Karvembu, R. Prabhakaran, K. Natarajan, Coord. Chem. Rev. 2005, 249, 911.

Discovery, Applications, and Catalytic Mechanisms of Shvo’s Catalyst

• B. L. Conley, M. K. Pennington-Boggio, E. Boz, T. J. Williams, Chem. Rev. 2010, 110 , 2294.

Anti-Markovnikov Hydration of Vinylarenes via Triple Relay Catalysis

Typical procedure (R = H): PdCl2(CH3CN)2 (10.4 mg), Shvo’s catalyst (43.6 mg), CuCl2 (10.8 mg) and 1,4-benzoquinone (43.2 mg) are weighed into a 20 mL vial under a nitrogen atmosphere, followed by the addition of i-PrOH (2 mL) and t-BuOH (4 mL). Styrene (41.7 mg) is added to the mixture followed by addition of H2O (8.1 micro-L). After the resulting mixture is stirred at 85 ºC for 6 h, it is diluted with pentane (6 mL) and filtered through a plug of silica gel followed by flushing with ethyl acetate (6 mL). The solvent is removed under vacuum, and the residue is purified by silica gel flash chromatography to give 2-phenylethyl alcohol (41 mg, 87 % yield).

• G. Dong, P. Teo, Z. K. Wickens, R. H. Grubbs, Science 2011, 333, 1609.

Synthesis of Aromatic Amines under Catalytic Transfer Hydrogenation Conditions

Typical procedure (entry 1): In a pressure tube under an argon atmosphere, the Shvo’s catalyst (22 mg), p-toluidine (429 mg), and hexylamine (202 mg) are dissolved in tert-amyl alcohol (0.5 ml). The pressure tube is fitted with a polytetrafluoroethylene cap and heated at 150 °C for 24 h in an oil bath. The solvent is removed in vacuo, and the crude product is purified by column chromatography (eluent: pentane/ethyl acetate) to give N-hexyl-4-methylaniline as colorless crystals (374 mg, 98 %).

• D. Hollmann, S. B hn, A. Tillack, M. Beller, Angew. Chem. Int. Edit. 2007, 46, 8291.