Dehydrogenation of 1-Phenylethanol Catalyzed by Nickel(II)diphosphine Complexes

Abstract

Catalytic efficacy of the nickel(II)-diphosphine systems in the dehydrogenation of 1-phenylethanol to acetophenone under acceptorless conditions was investigated. Steric and electronic factors of the phosphine ligands were found to play an important role in the catalysis, while the nature of the base used and the reaction conditions, viz. time, tempe rature, and stoichiometry, have also shown major influence. Based on the preliminary analysis, a homogeneous pathway, perhaps involving nickel hydride species, was proposed. Due to the gradual disintegration of the catalytic species, deterioration of catalytic activity was observed resulting into low to moderate conversions. Among the series of catalysts examined, the highest conversion of 52% was exhibited by the catalyst C4, dichloro(1,2-bis(diphenylphosphino)ethane)nickel(II) (5 mol%), when loaded with 50 mol% of sodium ethoxide in toluene at 120 °C.

Keywords

• acceptorless dehydrogenation
• dehydrogenation of alcohol
• nickel (ii) catalyst
• 1,2 bis(alkyl/arylphosphino)alkane. homogeneous catalysis
• catalyst disintegration.