Catalytic Hydrogenation of Styrene Oxide with Cationic Rhodium Complexes

Article abstract of DOI:10.1021/jo00324a016

Catalytic hydrogenation of styrene oxide with cationic rhodium complexes was investigated to develop its selective conversion into the specific alcohol. β-Phenylethyl alcohol and phenylacetaldehyde were rather selectively produced without either α-phenylethyl alcohol or acetophenone through a selective antinormal fission of the epoxide ring.The catalytic activity and selectivity were found to depend strongly on the ligand, the activity for the formation of alcohol decreasing in the order, PEt3 > PMe3 <*> PPh3 >> diphos.The highest yield, achieved by the PEt3 complex, reached as high as 82percent after 8 h of reaction.A possible mechanism was proposed to explain the selective formation of β-phenylethyl alcohol and the role of water as a cocatalyst in the catalytic hydrogenation.