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Mesoporous phenolic resin catalysts and their use in asymmetric epoxidation and aldol reactions

An Verberckmoes (UGent) , Jeroen De Decker (UGent) , Thomas Bogaerts (UGent) and Pascal Van Der Voort (UGent)
Author
Organization
Abstract
Ordered mesoporous phenolic resins are an advanced class of ultra-stable mesoporous materials that offer potential applications in the field of catalysis. Two select examples of asymmetric catalysis will be presented. First, the Jacobsen catalyst N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese (III) chloride is covalently immobilized and highly dispersed on mesoporous phenolic resins through a direct and simple procedure. This novel catalytic system shows high catalytic activity and excellent enantioselectivity in the asymmetric epoxidation of diline. The heterogeneized Jacobsen catalyst is demonstrated to be a re-usable and zero-leaching catalyst system. In a second example, the mesoporous phenolic resins were functionalized with sulphonic acid groups and acted as novel support for the non-covalent immobilization of a L-phenylalanine derived chiral diamine organocatalyst for asymmetric aldol reactions. The immobilization is established by an acid-base interaction between the sulphonic acid group and the amine function. The acidity and in particular the electronic withdrawing environment of the sulphonic acid groups influence enormously the catalytic performance of the non-covalent immobilized chiral diamine catalyst.
Keywords
phenolic resin, porous materials, salen complex, aldol reactions, chiral epoxidation, sulphonation

Citation

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Chicago
Verberckmoes, An, Jeroen De Decker, Thomas Bogaerts, and Pascal Van Der Voort. 2014. “Mesoporous Phenolic Resin Catalysts and Their Use in Asymmetric Epoxidation and Aldol Reactions.” In BIT’s 5th Annual Global Congress of Catalysis 2014 : Conference Abstract Book.
APA
Verberckmoes, A., De Decker, J., Bogaerts, T., & Van Der Voort, P. (2014). Mesoporous phenolic resin catalysts and their use in asymmetric epoxidation and aldol reactions. BIT’s 5th annual global congress of catalysis 2014 : conference abstract book. Presented at the BIT’s 5th Annual Global Congress of Catalysis 2014.
Vancouver
1.
Verberckmoes A, De Decker J, Bogaerts T, Van Der Voort P. Mesoporous phenolic resin catalysts and their use in asymmetric epoxidation and aldol reactions. BIT’s 5th annual global congress of catalysis 2014 : conference abstract book. 2014.
MLA
Verberckmoes, An, Jeroen De Decker, Thomas Bogaerts, et al. “Mesoporous Phenolic Resin Catalysts and Their Use in Asymmetric Epoxidation and Aldol Reactions.” BIT’s 5th Annual Global Congress of Catalysis 2014 : Conference Abstract Book. 2014. Print.
@inproceedings{5713760,
  abstract     = {Ordered mesoporous phenolic resins are an advanced class of ultra-stable mesoporous materials that offer potential applications in the field of catalysis. Two select examples of asymmetric catalysis will be presented. First, the Jacobsen catalyst N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese (III) chloride is covalently immobilized and highly dispersed on mesoporous phenolic resins through a direct and simple procedure. This novel catalytic system shows high catalytic activity and excellent enantioselectivity in the asymmetric epoxidation of diline. The heterogeneized  Jacobsen catalyst is demonstrated to be a re-usable and zero-leaching catalyst system. In a second example, the mesoporous phenolic resins were functionalized with sulphonic acid groups and acted as novel support for the non-covalent immobilization of a L-phenylalanine derived chiral diamine organocatalyst for asymmetric aldol reactions. The immobilization is established by an acid-base interaction between the sulphonic acid group and the amine function. The acidity and in particular the electronic withdrawing environment of the sulphonic acid groups influence enormously the catalytic performance of the non-covalent immobilized chiral diamine catalyst.},
  author       = {Verberckmoes, An and De Decker, Jeroen and Bogaerts, Thomas and Van Der Voort, Pascal},
  booktitle    = {BIT's 5th annual global congress of catalysis 2014 : conference abstract book},
  language     = {eng},
  location     = {Qingdao, PR China},
  title        = {Mesoporous phenolic resin catalysts and their use in asymmetric epoxidation and aldol reactions},
  year         = {2014},
}