A new method for the chemoselective reduction of aldehydes and ketones using boron tri-isopropoxide, B(O𝑖Pr)3: Comparison with boron tri-ethoxide, B(OEt)3

Journal of Chemical Sciences

Burcu Uysal¹  Birsen S Oksal1¹ 

[1] Department of Chemistry, Akdeniz University, 07058, Antalya, Turkey$$

关键词: Boron tri-iso-propoxide;    boron tri-ethoxide;    chemoselective reduction;    allylic alcohols;    Meerwein-Ponndorf-Verley reduction.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

A chemoselective Meerwein-Ponndorf-Verley reduction process of various aliphatic and allylic 𝛼,𝛽-unsaturated aldehydes and ketones is described. This chemoselective reduction is catalysed by boron triisopropoxide B(O𝑖Pr)3. Kinetics of reduction of aldehydes and ketones to corresponding alcohols were also examined and rate constant of each carbonyl compounds were measured. Rate constant and reduction yield of each carbonyl compounds in the presence of B(O𝑖Pr)3 were compared with those in the presence of B(OEt)3. The alcohols that are the reduction product were analysed by GC-MS. The rate constants and alcohol yields were found to be higher with B(OEt)3 than with B(O𝑖Pr)3. 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.

【 授权许可】

Unknown