Kinetics of catalytic Meerwein-Ponndorf-Verley reduction of aldehydes and ketones using boron triethoxide |
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Authors: | Burcu Uysal Birsen S Buyuktas |
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Institution: | (1) Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628 BL Delft, The Netherlands |
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Abstract: | Catalytic 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. |
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