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

Uysal B., Oksal B. Ş.

JOURNAL OF CHEMICAL SCIENCES, cilt.123, sa.5, ss.681-685, 2011 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 123 Sayı: 5
  • Basım Tarihi: 2011
  • Dergi Adı: JOURNAL OF CHEMICAL SCIENCES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED)
  • Sayfa Sayıları: ss.681-685
  • Anahtar Kelimeler: Boron tri-iso-propoxide, boron tri-ethoxide, chemoselective reduction, allylic alcohols, Meerwein-Ponndorf-Verley reduction, MEERWEIN-PONNDORF-VERLEY, OPPENAUER REACTIONS, SELECTIVE CATALYST, ALUMINUM, ALCOHOLS, ZIRCONIA, REAGENTS
  • Akdeniz Üniversitesi Adresli: Evet

Özet

A chemoselective Meerwein-Ponndorf-Verley reduction process of various aliphatic and allylic alpha,beta-unsaturated aldehydes and ketones is described. This chemoselective reduction is catalysed by boron tri-isopropoxide B(O-i Pr)(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(O-i Pr)(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(O-i Pr)(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.
A new method for the chemoselective reduction of aldehydes and ketones using boron tri-isopropoxide, B((OPr)-Pr-i)(3): Comparison with boron tri-ethoxide, B(OEt)(3)

By:Uysal, B (Uysal, Burcu)[ 1 ] ; Oksal, BS (Oksal, Birsen S.)[ 1 ]

 

JOURNAL OF CHEMICAL SCIENCES

 

Volume: 123

 

Issue: 5

 

Pages: 681-685

Published: SEP 2011

View Journal Information

Abstract

A chemoselective Meerwein-Ponndorf-Verley reduction process of various aliphatic and allylic alpha,beta-unsaturated aldehydes and ketones is described. This chemoselective reduction is catalysed by boron tri-isopropoxide B(O-i Pr)(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(O-i Pr)(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(O-i Pr)(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.