Chiral (VO)-O-IV-Sal-Indanol complex over modified SBA-15: an efficient, reusable enantioselective catalyst for asymmetric sulfoxidation reaction

TitleChiral (VO)-O-IV-Sal-Indanol complex over modified SBA-15: an efficient, reusable enantioselective catalyst for asymmetric sulfoxidation reaction
Publication TypeJournal Article
Year of Publication2013
AuthorsLazar, A, Sharma, P, Singh, AP
JournalMicroporous and Mesoporous Materials
Volume170
Pagination331-339
Date PublishedAPR
ISSN1387-1811
Keywords(1R, 2S)-(+)-Cis-1-amino-2-indanol, Asymmetric sulfoxidation, Heterogeneous vanadium complex, Mesoporous, Thioanisole
Abstract

A reusable, mesoporous, heterogeneous vanadium complex, (VO)-O-IV-Sal-Ind-SBA-15 has been synthesized first time from (1R,2S)-(+)-Cis-1-amino-2-indanol for enantioselective sulfoxidation reaction. The physico-chemical properties of the functionalized catalyst were analyzed by a series of characterization techniques like XRD, N-2 sorption measurement isotherm, TEM, FT-IR, XPS, EPR, DRS UV-Visible, ICP-OES and solid & liquid state C-13, Si-29 and V-51 NMR spectroscopy. Powder X-ray diffraction patterns, TEM and N-2 physisorption analysis confirmed the retention of mesoporous structure after various modifications. Solid-state NMR (C-13 CP-MAS NMR, Si-29 MAS NMR) and FT-IR analysis certified the integrity of organo-catalyst residing inside the pore channels of the mesoporous support. Further, XPS, EPR, V-51 NMR and DRS UV-Visible analyses help to find out the oxidation state and coordination environment of vanadium in (VO)-O-IV-Sal-Ind-SBA-15. Catalytic evaluation in asymmetric sulfoxidation reaction of sulfides indicated that VOIV-Sal-Ind-SBA-15 exhibited higher catalytic activity, stability, reusability and comparable enantioselectivity than SBA-15, PrNH2-SBA-15, neat (VO)-O-IV-Sal-Indanol complex and without catalyst. The effect of different catalysts, temperature, solvents and substrates on sulfoxidation reaction were examined in order to optimize the conversion and enantioselectivity of thioanisoles to sulfoxides. Crown Copyright (C) 2012 Published by Elsevier Inc. All rights reserved.

DOI10.1016/j.micromeso.2012.12.014
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.27
Divison category: 
Catalysis and Inorganic Chemistry