Kinetics of catalytic Meerwein-Ponndorf-Verley reduction of aldehydes and ketones using boron triethoxide

Abstract

AbstractCatalytic Meerwein-Ponndorf-Verley (MPV) reduction of various aliphatic, aromatic, and unsaturated aldehydes and ketones to corresponding alcohols (analyzed by GC-MS) in the presence of boron triethoxide (B(OEt)3) were studied. Kinetics of this reduction reaction was also studied and the respective rate constants were determined. It was found that B(OEt)3 catalyzes the reduction of aliphatic aldehydes and ketones to alcohols at room temperature while aromatic aldehydes and ketones were not reduced under the same conditions. In addition, MPV reduction using B(OEt)3 was found to be chemoselective as unsaturated aldehydes and ketones afforded the corresponding alcohols without affecting unsaturated groups. The mechanism proposed involves a six-membered transition state in which both the alcohol and the carbonyl are coordinated to the same boron centre of a boron alkoxide catalyst.