Chemoselective reduction of alpha,beta-unsaturated aldehydes and ketones over mesoporous B(O (i) Pr)(3)-MCM-41 catalyst via MPV reduction process: preparation, characterization and catalytic application

Uysal B., Aksu Y., Oksal B. Ş.

JOURNAL OF POROUS MATERIALS, vol.20, no.1, pp.115-127, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 1
  • Publication Date: 2013
  • Doi Number: 10.1007/s10934-012-9580-3
  • Journal Name: JOURNAL OF POROUS MATERIALS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.115-127
  • Keywords: Allylic alcohols, Heterogeneous catalysis, alpha,beta-Unsaturated ketones and aldehydes, MPV reduction, MCM-41, MEERWEIN-PONNDORF-VERLEY, BORON TRI-ISOPROPOXIDE, OPPENAUER REACTIONS, HYDROGEN-TRANSFER, ALLYLIC ALCOHOLS, SILICA, MCM-41, ZIRCONIUM, COMPLEXES
  • Akdeniz University Affiliated: Yes

Abstract

Chemoselective reduction of alpha,beta-unsaturated aldehydes and ketones over mesoporous B(O (i) Pr)(3)-MCM-41 catalyst via MPV reduction process: preparation, characterization and catalytic application

By:Uysal, B (Uysal, Burcu)[ 1 ] ; Aksu, Y (Aksu, Yilmaz)[ 2 ] ; Oksal, BS (Oksal, Birsen S.)[ 1 ]

 

JOURNAL OF POROUS MATERIALS

 

Volume: 20

 

Issue: 1

 

Pages: 115-127

DOI: 10.1007/s10934-012-9580-3

Published: FEB 2013

View Journal Information

Abstract

Boron alkoxide-containing ordered mesoporous silica material (B(O (i) Pr)(3)-MCM-41) was prepared by the grafting method. The obtained B(O (i) Pr)(3)@MCM-41 composite materials were fully characterized in details by PXRD, FT-IR-, B-11-NMR-, Si-29-NMR-, C-13-NMR-spectroscopies, scanning electron microscopy, EDX, transmission electron microscopy techniques, N-2 adsorption-desorption isotherms and Inductively coupled plasma-optical emission spectroscopy analyses, demonstrating the successful homogenous distribution of the B(O (i) Pr)(3) catalyst in the MCM-41 support. The as-prepared new materials were successfully applied in the chemoselective Meerwein-Ponndorf-Verley reduction of alpha,beta-unsaturated carbonyl compounds. In the reduction of alpha,beta-unsaturated aldehydes and ketones, which can not be reduced by usual catalysts, a very high selectivity, especially for the reduction of allylic aldehydes and ketones could be obtained. In most cases no side product formation could be observed. The catalyst was found to be encouraging as a heterogeneous catalyst as the yield was almost unchanged after up to six cycles. No leaching of the grafted boron tri-isopropoxide into the reaction mixture could be detected.

 

Boron alkoxide-containing ordered mesoporous silica material (B(O (i) Pr)(3)-MCM-41) was prepared by the grafting method. The obtained B(O (i) Pr)(3)@MCM-41 composite materials were fully characterized in details by PXRD, FT-IR-, B-11-NMR-, Si-29-NMR-, C-13-NMR-spectroscopies, scanning electron microscopy, EDX, transmission electron microscopy techniques, N-2 adsorption-desorption isotherms and Inductively coupled plasma-optical emission spectroscopy analyses, demonstrating the successful homogenous distribution of the B(O (i) Pr)(3) catalyst in the MCM-41 support. The as-prepared new materials were successfully applied in the chemoselective Meerwein-Ponndorf-Verley reduction of alpha,beta-unsaturated carbonyl compounds. In the reduction of alpha,beta-unsaturated aldehydes and ketones, which can not be reduced by usual catalysts, a very high selectivity, especially for the reduction of allylic aldehydes and ketones could be obtained. In most cases no side product formation could be observed. The catalyst was found to be encouraging as a heterogeneous catalyst as the yield was almost unchanged after up to six cycles. No leaching of the grafted boron tri-isopropoxide into the reaction mixture could be detected.