2. Academic Validation
  3. Mechanochemical Lignin-Mediated Strecker Reaction

Mechanochemical Lignin-Mediated Strecker Reaction

  • Molecules. 2017 Jan 17;22(1):146. doi: 10.3390/molecules22010146.
Saumya Dabral 1,  Mathias Turberg 2,  Andrea Wanninger 3,  Carsten Bolm 4,  José G Hernández 5
Affiliations

Affiliations

  • 1 Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. [email protected].
  • 2 Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. [email protected].
  • 3 Angewandte Organische Chemie, Hochschule Niederrhein, University of Applied Sciences, Adlerstr. 32, D-47798 Krefeld, Germany. [email protected].
  • 4 Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. [email protected].
  • 5 Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. [email protected].
PMID: 28106742 DOI: 10.3390/molecules22010146
Abstract

A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by lignocellulosic biomass as additives. Particularly, commercially available Kraft lignin was found to be the best activator for the addition of cyanide to the in situ formed imines. A comparative study of the 31P-NMR (Nuclear Magnetic Resonance) along with IR (Infrared) data analysis for the Kraft lignin and methylated Kraft lignin samples ascertained the importance of the free hydroxyl groups in the activation of the mechanochemical reaction. The solvent-free mechanochemical Strecker reaction was then coupled with a lactamization process leading to the formation of the N-benzylphthalimide (5a) and the isoindolinone derivative 6a.

Keywords

Strecker reaction; ball milling; lignin; mechanochemistry; multicomponent reactions.

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