Journal of Materials Science

, Volume 48, Issue 17, pp 5990–6000 | Cite as

Simultaneous synthesis of modified Binol-periodic mesoporous organosilica SBA-15 type material. Application as catalysts in asymmetric sulfoxidation reactions

  • V. Morales
  • J. A. Villajos
  • R. A. García


The synthesis of a chiral periodic mesoporous organosilica (chiral PMO) SBA-15 type, using a bis-silylated Binol precursor, has been studied through two different heterogenization routes. On the one hand, the immobilization of a (R)-(+)-1,1′-bi-2-naphthol (Binol) derivative was accomplished by following a standard multistep synthesis methodology. On the other hand, a new route consisting of an easy one-step synthesis was developed achieving a simultaneous formation of mesoporous structure and Binol chiral ligand immobilization in the walls. The addition of KCl “salting out” electrolytes favored the micellization, obtaining the well-ordered chiral PMO materials. The thioanisole asymmetric oxidation reaction was used to validate the enantio-catalysts activity. The materials synthesized by the multistep method reached yield and enantiomeric excess of 41 and 15 %, respectively, while the synthesized one-pot chiral PMO materials achieved up to 58 and 42 %, respectively. This difference could be attributed to a more homogenous distribution of the chiral moiety as well as the simultaneous micellization and formation of the siliceous mesostructure, in the one-pot procedure. This promotes higher reagents accessibility to the active center, and therefore an enhancement of the chiral induction. Thereby, materials with Binol ligand incorporated into the three-dimensional silica framework were successfully accomplished.


Multistep Method Chiral Ligand Binol Thioanisole Asymmetric Catalysis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



The financial support of the Spanish government (CTQ2008-05909/PPQ and CTQ2011-22707) is gratefully acknowledged.


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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  1. 1.Department of Chemical and Environmental Technology, ESCETUniversidad Rey Juan CarlosMóstolesSpain

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