Synlett 2018; 29(15): 1983-1988
DOI: 10.1055/s-0037-1610235
letter
© Georg Thieme Verlag Stuttgart · New York

Exploration of the Role of Double Schiff Bases as Catalytic Intermediates in the Knoevenagel Reaction of Furanic Aldehydes: Mechanistic Considerations

Authors

  • Jack van Schijndel  *

    a   Research Group Biopolymers/Green Chemistry, Centre of Expertise BioBased Economy, Avans University of Applied Science, Lovensdijkstraat 61, 4818 AJ Breda, The Netherlands   Email: jam.vanschijndel@avans.nl
    b   Department of Chemical Engineering and Chemistry, Lab of Chemical Reactor Engineering/Polymer Reaction Engineering, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands
  • Luiz Alberto Canalle

    a   Research Group Biopolymers/Green Chemistry, Centre of Expertise BioBased Economy, Avans University of Applied Science, Lovensdijkstraat 61, 4818 AJ Breda, The Netherlands   Email: jam.vanschijndel@avans.nl
  • Dennis Molendijk

    a   Research Group Biopolymers/Green Chemistry, Centre of Expertise BioBased Economy, Avans University of Applied Science, Lovensdijkstraat 61, 4818 AJ Breda, The Netherlands   Email: jam.vanschijndel@avans.nl
  • Jan Meuldijk

    b   Department of Chemical Engineering and Chemistry, Lab of Chemical Reactor Engineering/Polymer Reaction Engineering, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands

The authors are grateful for the financial support from Netherlands Organization for Scientific Research (NWO) (grant 023.007.020 awarded to Jack van Schijndel).
Further Information

Publication History

Received: 12 April 2018

Accepted after revision: 17 July 2018

Publication Date:
13 August 2018 (online)


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Abstract

This paper presents mechanistic considerations on an efficient, green, and solvent-free Knoevenagel procedure for the chemical transformation of furanic aldehydes into their corresponding α,β-unsaturated compounds. In the proposed mechanism furanic aldehydes react with ammonia, released from ammonium salts, to form a catalytically active double Schiff base. The catalytic intermediates involved in the condensation step are characterized.

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