Oxygenation of aromatic hydrocarbons with hydrogen peroxide catalyzed by rhodium carbonyl complexes

Abstract

Abstract Hexanuclear rhodium carbonyl cluster, Rh 6 (CO) 16 , catalyzes benzene hydroxylation with hydrogen peroxide in acetonitrile solution. Phenol and (at lower concentration) quinone are formed with the maximum attained total yield and turnover number 17% and 683, respectively. Certain other rhodium carbonyl complexes, containing cyclopentadienyl ligands, Rh 2 Cp 2 (CO) 3 and Rh 3 (CpMe) 3 (CO) 3 , are less efficient catalysts. Cyclopentadienyl derivatives of rhodium which do not contain the carbonyl ligands, Rh(CpMe 5 )(CH 2 CH 2 ) 2 , RhCp(cyclooctatetraene) and Rh 2 Cp 2 (cyclooctatetraene) turned out to be absolutely inactive in the benzene hydroxylation. Styrene is transformed into benzaldehyde and (at lower concentration) acetophenone and 1‐phenylethanol. Copyright © 2008 John Wiley & Sons, Ltd.