Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases

Tassi, Marco; Bartollini, Elena; Adriaensens, Peter; Bianchi, Luca; Barkakaty, Balaka; Carleer, Robert; Chen, Jihua; Hensley, Dale K.; Marrocchi, Assunta; Vaccaro, Luigi

doi:10.1039/C5RA21140A

Title: Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases

Abstract

In view of searching for efficient polymeric supports for organic bases to be used in environmentally friendly reaction conditions, novel gel-type cross-linked polystyrenes functionalized with diethylamine and 1,5,7-triazabicyclo[4.4.0]dec-5-ene, have been prepared. Moreover, the structural properties and morphology of these catalysts have been determined by extensive solid state NMR experiments, FTIR spectroscopy and SEM/TEM microscopy. SPACeR-supported bases were found to exhibit high catalytic activity in the epoxide ring opening by phenols. Finally, a range of β-substituted alcohols have been readily and regioselectively synthesized.

Authors:

Tassi, Marco ^[1]; Bartollini, Elena ^[2]; Adriaensens, Peter ^[1]; Bianchi, Luca ^[2]; Barkakaty, Balaka ^[3]; Carleer, Robert ^[1]; Chen, Jihua ^[3]; Hensley, Dale K. ^[3]; Marrocchi, Assunta ^[2]; Vaccaro, Luigi ^[2]

Hasselt Univ., Diepenbeek (Belgium)
Univ. of Perugia (Italy)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Publication Date:: Mon Dec 07 00:00:00 EST 2015

Research Org.:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1265894

Grant/Contract Number:: AC05-00OR22725

Resource Type:: Accepted Manuscript

Journal Name:: RSC Advances

Additional Journal Information:: Journal Volume: 5; Journal Issue: 130; Journal ID: ISSN 2046-2069

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Tassi, Marco, Bartollini, Elena, Adriaensens, Peter, Bianchi, Luca, Barkakaty, Balaka, Carleer, Robert, Chen, Jihua, Hensley, Dale K., Marrocchi, Assunta, and Vaccaro, Luigi. Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases.  United States: N. p., 2015. 
Web.  doi:10.1039/C5RA21140A.

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                    Tassi, Marco, Bartollini, Elena, Adriaensens, Peter, Bianchi, Luca, Barkakaty, Balaka, Carleer, Robert, Chen, Jihua, Hensley, Dale K., Marrocchi, Assunta, & Vaccaro, Luigi. Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases.  United States.  https://doi.org/10.1039/C5RA21140A

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                    Tassi, Marco, Bartollini, Elena, Adriaensens, Peter, Bianchi, Luca, Barkakaty, Balaka, Carleer, Robert, Chen, Jihua, Hensley, Dale K., Marrocchi, Assunta, and Vaccaro, Luigi. Mon .  
"Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases".  United States.  https://doi.org/10.1039/C5RA21140A.  https://www.osti.gov/servlets/purl/1265894.

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@article{osti_1265894,

  title        = {Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases},

  author       = {Tassi, Marco and Bartollini, Elena and Adriaensens, Peter and Bianchi, Luca and Barkakaty, Balaka and Carleer, Robert and Chen, Jihua and Hensley, Dale K. and Marrocchi, Assunta and Vaccaro, Luigi},

  abstractNote = {In view of searching for efficient polymeric supports for organic bases to be used in environmentally friendly reaction conditions, novel gel-type cross-linked polystyrenes functionalized with diethylamine and 1,5,7-triazabicyclo[4.4.0]dec-5-ene, have been prepared. Moreover, the structural properties and morphology of these catalysts have been determined by extensive solid state NMR experiments, FTIR spectroscopy and SEM/TEM microscopy. SPACeR-supported bases were found to exhibit high catalytic activity in the epoxide ring opening by phenols. Finally, a range of β-substituted alcohols have been readily and regioselectively synthesized.},

  doi          = {10.1039/C5RA21140A},

  journal      = {RSC Advances},

  number       = 130,

  volume       = 5,

  place        = {United States},

  year         = {Mon Dec 07 00:00:00 EST 2015},

  month        = {Mon Dec 07 00:00:00 EST 2015}

}

Copy to clipboard

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Works referencing / citing this record:

Synthesis of β-Cyano Ketones Promoted by a Heterogeneous Fluoride Catalyst
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Strappaveccia, Giacomo; Angelini, Tommaso; Bianchi, Luca
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Title: Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases

Abstract

Citation Formats

Rational Approach to Polymer-Supported Catalysts: Synergy between Catalytic Reaction Mechanism and Polymer Design journal, September 2008

Development of new methods toward efficient immobilization of chiral catalysts journal, July 2007

Chiral Salen Complexes: An Overview to Recoverable and Reusable Homogeneous and Heterogeneous Catalysts journal, September 2006

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Synthesis of Mesoporous Carbons Derived from Hypercrosslinking of Divinylbenzene – 4-Vinylbenzyl Chloride Resin journal, November 2007

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Chiral Salen Complexes: An Overview to Recoverable and Reusable Homogeneous and Heterogeneous Catalysts journal, December 2006

Three-membered ring systems book, January 2009

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journal, September 2006

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journal, July 2006

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E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds
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Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide
journal, July 1963

New supports for solid-phase organic synthesis: development of polystyrene resins containing tetrahydrofuran derived cross-linkers
journal, August 1999

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journal, January 2001

Epoxidöffnungskaskaden zur Synthese polycyclischer Polyether-Naturstoffe
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book, January 2009

Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols
journal, January 2013

2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2- diazaphosphorine Supported on Polystyrene (PS-BEMP) as an Efficient Recoverable and Reusable Catalyst for the Phenolysis of Epoxides under Solvent-Free Conditions
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Size Selectivity of a Copper Metal-Organic Framework and Origin of Catalytic Activity in Epoxide Alcoholysis
journal, October 2009

Copper(II) Tetrafluoroborate Catalyzed Ring-Opening Reaction of Epoxides with Alcohols at Room Temperature
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journal, January 2014

An E-Factor Minimized Protocol for a Sustainable and Efficient Heck Reaction in Flow
journal, October 2014

A Convenient Method for the Preparation of 4-Aryloxyphenols
journal, January 1991

Polymer-Supported Bases. XI. Esterification and Alkylation in the Presence of Polymer-Supported Bicyclic Amidine or Guanidine Moieties
journal, March 1992

Synthesis of Mesoporous Carbons Derived from Hypercrosslinking of Divinylbenzene – 4-Vinylbenzyl Chloride Resin
journal, November 2007

Synthesis of Davankov-type hypercrosslinked resins using different isomer compositions of vinylbenzyl chloride monomer, and application in the solid-phase extraction of polar compounds: Davankov-Type Hypercrosslinked Resins
journal, March 2005

Anion-exchange resins from vinylbenzyl choride: control of hydrolysis during polymerization
journal, April 1996

Solid-State ¹³ C MAS NMR Studies of Hyper-Cross-Linked Polystyrene Resins
journal, January 1996

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journal, May 2005

Recycling Asymmetric Hydrogenation Catalysts by Their Immobilization onto Ion-Exchange Resins
journal, October 2006

Chiral Salen Complexes: An Overview to Recoverable and Reusable Homogeneous and Heterogeneous Catalysts
journal, December 2006

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